Skip to main content
SpringerLink
Log in
Book cover

Small Ring Compounds in Organic Synthesis II pp 77–151Cite as

Cyclopropenes and methylenecylopropanes as multifunctional reagents in transition metal catalyzed reactions

  • Conference paper
  • First Online:

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 135))

Abstract

The tremendous potential of cyclopropenes and methylene-cyclopropanes as multifunctional reagents in organic syntheses has only been recognized in the last decade. The use of transition metal catalysts allows an effective control of their transformations enabling highly selecitive syntheses ranging from three- to sevenmembered carbocycles. The activities in this field are summarized in this review for the first time with an emphasis on the preparative aspects of this work.

This is a preview of subscription content, log in via an institution.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

6 References

  1. Köster, R., Arora, S., Binger, P.: Angew. Chem. 81, 186 (1969); Angew. Chem. Int. Ed. Engl. 8, 205 (1969)

    Google Scholar 

  2. Köster, R., Arora, S., Binger, P.: Synthesis 322 (1971)

    Google Scholar 

  3. Salaün, J. R., Conia, J. M.: J. Chem. Soc. Chem. Commun. 1579 (1971)

    Google Scholar 

  4. Caubere, P., Coudert, G.: Bull. Soc. Chim. France, 2234 (1971)

    Google Scholar 

  5. Köster, R., Arora, S., Binger, P.: Liebigs Ann. Chem. 1219 (1973)

    Google Scholar 

  6. Arora, S., Binger, P.: Synthesis 801 (1974)

    Google Scholar 

  7. Arora, S., Binger, P., Köster, R.: Synthesis 146 (1973)

    Google Scholar 

  8. Binger, P.: Synthesis 190 (1974)

    Google Scholar 

  9. Magid, R. M., Clarke, T. C., Duncan, C. D.: J. Org. Chem. 36, 1320 (1971)

    Google Scholar 

  10. Yoshida, Z., Miyahara, H.: Chem. Lett. 335 (1972)

    Google Scholar 

  11. Huisgen, R.: Angew. Chem. 75, 742 (1963); Angew. Chem. Int. Ed. Engl. 2, 633 (1963)

    Google Scholar 

  12. Kellogg, R. M.: Tetrahedron 32, 2165 (1976)

    Google Scholar 

  13. Carter, F. L., Frampton, V. L.: Chem. Rev. 64, 497 (1964)

    Google Scholar 

  14. Closs, G. L.: Adv. Alicyclic Chem. 1, 53 (1966)

    Google Scholar 

  15. Wendisch, D.: Houben/Weyl 4/3, 679 (1971)

    Google Scholar 

  16. Grigorova, T. N.: Sovrem. Probl. Org. Khim. 3, 100 (1974); CA 82: 154586a

    Google Scholar 

  17. Allen, F. H.: Tetrahedron 38, 645 (1982)

    Google Scholar 

  18. Deem, M. L.: Synthesis 675 (1972)

    Google Scholar 

  19. Schuchardt, U., dos Santos Filho, P. F.: Cienc. Cult. (Sao Paulo) 30, 161 (1978): CA 89: 75269r

    Google Scholar 

  20. Padwa, A.: Acc. Chem. Res. 12, 310 (1979)

    Google Scholar 

  21. Padwa, A.: Organic Photochem. 4, 261 (1979)

    Google Scholar 

  22. Binger, P., Cetinkaya, B., Doyle, M. J., Germer, A., Schuchardt, U.: Fundam. Res. Homogeneous Catal. 3, 271 (1979)

    Google Scholar 

  23. Deem, M. L.: Synthesis 701 (1982)

    Google Scholar 

  24. see ref. 8

    Google Scholar 

  25. Nefedov, O. M., Dolgii, I. E., Bulusheva, E. V., Shteinshneider, A. Ya.: Izv. Akad. Nauk SSSR, 1535 (1979); Engl. transl. 28, 1422 (1979)

    Google Scholar 

  26. Dijachenko, A. I., Agre, S. A., Rudashevskaya, T. Y., Shafran, R. M., Nefedov, O. M.: Izv. Akad. Nauk SSSR, 2820 (1984); Engl. transl. 33, 2585 (1984)

    Google Scholar 

  27. Binger, P.: unpublished results

    Google Scholar 

  28. Martel, B., Hiriat, J. M.: Synthesis 201 (1972)

    Google Scholar 

  29. Demjanov, N. Y., Doyarenko, M. N.: Bull. Acad. Sciences USSR 16, 297 (1922)

    Google Scholar 

  30. Weigert, F. J., Baird, R. L., Shapley, J. R.: J. Am. Chem. Soc. 92, 6630 (1970)

    Google Scholar 

  31. Hoffmann, H. M. R.: Angew. Chem. 81, 597 (1969); Angew. Chem. Int. Ed. Engl. 8, 556 (1969)

    Google Scholar 

  32. Closs, G. L., Closs, L. E., Böll, W. A.: J. Am. Chem. Soc. 85, 3796 (1963)

    Google Scholar 

  33. v. R. Schleyer, P., Williams, J. E., Blanchard, K. R.: J. Am. Chem. Soc. 92, 2377 (1970)

    Google Scholar 

  34. Bastiansen, O., Fritsch, F. N., Hedberg, K.: Acta Cryst. 17, 538 (1964)

    Google Scholar 

  35. Wiberg, K. B., Ellison, G. B., Wendoloski, J. J., Pratt, W. E., Harmony, M. D.: J. Am. Chem. Soc. 100, 7837 (1978)

    Google Scholar 

  36. Wiberg, K. B., Bartley, W. J.: J. Am. Chem. Soc. 82, 6375 (1960)

    Google Scholar 

  37. Greenberg, A., Liebman, J. F.: Strained Organic Molecules, Academic Press, New York (1978)

    Google Scholar 

  38. Davis, J. H., Goddard III, W. A., Berman, R. G.: J. Am. Chem. Soc. 99, 2427 (1977)

    Google Scholar 

  39. York, E. J., Dittmar, W., Stevenson, J. R., Bergman, R. G.: J. Am. Chem. Soc., 95, 5680 (1973)

    Google Scholar 

  40. de Boer, J. J., Bright, D.: J. Chem. Soc. Dalton Trans. 662 (1975)

    Google Scholar 

  41. Binger, P., Doyle, M. J., McMeeking, J., Krüger, C., Tsay, Y.-H.: J. Organomet. Chem. 135, 405 (1977)

    Google Scholar 

  42. Binger, P., Doyle, M. J.: J. Organomet. Chem. 162, 195 (1978)

    Google Scholar 

  43. Peganova, T. A., Petrovskii, P. V., Isaeva, L. S., Kravtsov, D. N., Furman, D. B., Kudryashev, A. V., Ivanov, A. O., Zotova, S. V., Bragin, O. V.: J. Organomet. Chem. 282, 283 (1985)

    Google Scholar 

  44. Binger, P., Büch, H. M., Benn, R., Mynott, R.: Angew. Chem. 94, 66 (1982); Angew. Chem. Int. Ed. Engl. 21, 62 (1982); Angew. Chem. Suppl. 153–160 (1982)

    Google Scholar 

  45. Cetinkaya, B., Binger, P., Krüger, C.: Chem. Ber. 115, 3414 (1982)

    Google Scholar 

  46. Binger, P., Cetinkaya, B., Krüger, C.: J. Organomet. Chem. 159, 63 (1978)

    Google Scholar 

  47. Newton, M. G., Pantaleo, N. S., King, R. B., Chu, C.-K.: J. Chem. Soc. Chem. Commun. 10 (1979)

    Google Scholar 

  48. Dettlaf, G., Behrens, U., Weiss, E.: Chem. Ber. 111, 3019 (1978)

    Google Scholar 

  49. Klimes, A., Weiss, E.: Chem. Ber., 115, 2175 (1982); ibid. 115, 2606 (1982)

    Google Scholar 

  50. Franck-Neumann, M., Dietrich-Buchecker, C., Khemiss, A. K.: J. Organomet. Chem. 220, 187 (1981)

    Google Scholar 

  51. Jens, K. J., Weiss, E.: Chem. Ber., 117, 2469 (1984)

    Google Scholar 

  52. Green, M., Norman, N. C., Orpen, A. G.: J. Organomet. Chem. 221, C11 (1981)

    Google Scholar 

  53. Barker, G. K., Carroll, W. E., Green, M., Welch, A. J.: J. Chem. Soc. Chem. Commun., 1071 (1980)

    Google Scholar 

  54. Büch, H. M., Krüger, C.: Acta Cryst. C40, 28 (1984)

    Google Scholar 

  55. Puddephatt, R. J.: Comments Inorg. Chem. 2, 69 (1982)

    Google Scholar 

  56. Wong, W., Singer, S. J., Pitts, W. D., Watkins, S. F., Baddley, W. H.: J. Chem. Soc. Chem. Commun. 672 (1972)

    Google Scholar 

  57. Visser, J. P., Ramakers-Blom, J. E.: J. Organomet. Chem. 44, C63 (1972)

    Google Scholar 

  58. Schaverien, C. J., Green, M., Orpen, A. G., Williams, I. D.: J. Chem. Soc. Chem. Commun. 912 (1982)

    Google Scholar 

  59. Lehmkuhl, H., Mehler, K.: Liebigs Ann. Chem., 2244 (1982); and cited lit. therein

    Google Scholar 

  60. Nesmeyanova, O. A., Kudryatseva, G. A.: Izv. Akad. Nauk SSSR, Ser. Khim., 2629 (1982); Engl. transl. 31, 2324 (1982)

    Google Scholar 

  61. Binger, P., Brinkmann, A.: unpublished results

    Google Scholar 

  62. Tolman, C. A.: Chem. Rev. 77, 313 (1977)

    Google Scholar 

  63. Franck-Neumann, M., Dietrich-Buchecker, C.: Tetrahedron Lett. 21, 671 (1980)

    Google Scholar 

  64. Matsui, Y., Orchin, M.: J. Organomet. Chem. 244, 369 (1983)

    Google Scholar 

  65. Kirmse, W.: Carbene Chemistry, Organic Chemistry, Monograph Series 1, 267 Academic Press New York (1971)

    Google Scholar 

  66. Stechl, H. H.: Angew. Chem. 75, 1176 (1963); Angew. Chem. Int. Ed. Engl. 2, 743 (1963)

    Google Scholar 

  67. Stechel, H. H.: Chem. Ber. 97, 2681 (1964)

    Google Scholar 

  68. Franck-Neumann, M., Lohmann, J. J.: Angew. Chem. 89, 331 (1977); Angew. Chem. Int. Ed. Engl. 16, 323 (1977)

    Google Scholar 

  69. Baird, M. S., Buxton, S. R., Whitley, J. S.: Tetrahedron Lett. 25, 1509 (1984)

    Google Scholar 

  70. Baird, M. S.: Tetrahedron Lett. 25, 4829 (1984)

    Google Scholar 

  71. Domnin, I. N., Kortikov, R. R., deMeijere, A.: Zh. Org. Khim. SSSR 19, 2206 (1982); Engl. transl. 19, 1921 (1983)

    Google Scholar 

  72. Boger, D. L., Brotherton, C. E.: Tetrahedron Lett. 25, 5611 (1984)

    Google Scholar 

  73. Binger, P., McMeeking, J.: Angew. Chem. 86, 518 (1974); Angew. Chem. Int. Ed. Engl. 13, 466 (1974)

    Google Scholar 

  74. Binger, P., McMeeking, J., Schäfer, H.: Chem. Ber. 117, 1551 (1984)

    Google Scholar 

  75. Tomilov, Yu. V., Bordakov, V. G., Tsvetkova, N. M., Dolgii, I. E., Nefedov, O. M.: Izv. Akad. Nauk SSSR, Ser. Khim., 2413 (1982); Engl. transl. 31, 2129 (1982)

    Google Scholar 

  76. Tomilov, Yu. V., Bordakov, V. G., Tsvetkova, N. M., Shteinshneider, A. Ya., Dolgii, I. E., Nefedov, O. M.: Izv. Akad. Nauk SSSR, Ser. Khim. 336 (1983); Engl. transl. 32, 300 (1983)

    Google Scholar 

  77. Dolgii, I. E., Tomilov, Yu. V., Shteinshneider, A. Yu., Nefedov, O. M.: Izv. Akad. Nauk Nauk SSSR, Ser. Khim. 700 (1983); Engl. transl. 32, 638 (1983)

    Google Scholar 

  78. Ito, Y., Yonezawa, K., Saegusa, T.: J. Org. Chem. 39, 1763 (1974)

    Google Scholar 

  79. Jolly, P. W., Wilke, G.: The Organic Chemistry of Nickel, Vol. 1, Academic Press, New York (1974)

    Google Scholar 

  80. Schipperijn, A. J., Lukas, J.: Tetrahedron Lett., 231 (1972)

    Google Scholar 

  81. idem, Recl. Trav. Chim. Pays-Bas 92, 572 (1973)

    Google Scholar 

  82. Binger, P., Schäfer, H.: Tetrahedron Lett., 4673 (1975)

    Google Scholar 

  83. Binger, P., Schäfer, H.: unpublished results

    Google Scholar 

  84. Binger, P., McMeeking, J., Schuchardt, U.: Chem. Ber. 113, 2372 (1980)

    Google Scholar 

  85. Binger, P., Schuchardt, U.: Chem. Ber. 114, 1649 (1981)

    Google Scholar 

  86. Bennett, M. J., Purdham, J. T., Takada, S., Masamune, S.: J. Am. Chem. Soc. 93, 4063 (1971)

    Google Scholar 

  87. Gassman, P. G., Johnson, T. H.: J. Am. Chem. Soc. 98, 861 (1976)

    Google Scholar 

  88. Dolgii, I. E., Tomilov, Yu. V., Tsvetkova, N. M., Bordakov, V. G., Nefedov, O. M.: Izv. Akad. Nauk SSSR, Ser. Khim. 958 (1983); Engl. transl. 32, 868 (1983)

    Google Scholar 

  89. Weiß, R., Schlierf, C.: Angew. Chem. 83, 887 (1971); Angew. Chem. Int. Ed. Engl. 10, 811 (1971)

    Google Scholar 

  90. Landheer, I. J., de Wolf, W. H., Bickelhaupt, F.: Tetrahedron Lett., 2813 (1974)

    Google Scholar 

  91. idem: ibid. 349 (1975)

    Google Scholar 

  92. Gröger, C., Musso, H., Roßnagel, I.: Chem. Ber. 113, 3621 (1980)

    Google Scholar 

  93. Stahl, K.-J., Hertzsch, W., Musso, H.: Liebigs Ann. Chem. 1985, 1474

    Google Scholar 

  94. Boger, D. L., Brotherton, C. E.: J. Am. Chem. Soc. 106, 805 (1984)

    Google Scholar 

  95. Komendantov, M. I., D'yakonov, I. A., Smirnova, T. S.: Zh. Org. Khim. 2, 559 (1966); J. Org. Chem. USSR 2, 562 (1966)

    Google Scholar 

  96. Komendantov, M. I., Kryuchkova, I. K., Domnin, I. N.: Zh. Org. Khim. 6, 631 (1970); J. Org. Chem. USSR 6, 630 (1970)

    Google Scholar 

  97. Komendantov, M. I., Smirnova, T. S., Domnin, I. N., Krakhmal'naya, L. A.: Zh. Org. Khim. 7, 2455 (1971); J. Org. Chem. USSR 7, 2551 (1971)

    Google Scholar 

  98. Komendantov, M. I., Domnin, I. N., Bulucheva, E. V.: Tetrahedron 31, 2495 (1975)

    Google Scholar 

  99. Komendantov, M. I., Domnin, I. N.: Zh. Org. Khim. 5, 1319 (1969); J. Org. Chem. 5, 1288 (1969)

    Google Scholar 

  100. Breslow, R.: Mol. Rearrangements 1, 257 Interscience Publishers, New York (1963)

    Google Scholar 

  101. Battiste, M. A., Halton, B., Grubbs, R. H.: J. Chem. Soc. Chem. Commun. 907 (1967)

    Google Scholar 

  102. Walker, J. A., Orchin, M.: ibid. 1239 (1968)

    Google Scholar 

  103. Padwa, A., Blacklock, T. J., Loza, R.: J. Am. Chem. Soc. 103, 2404 (1981)

    Google Scholar 

  104. Binger, P., Brinkmann, A.: Chem. Ber. 111, 2689 (1978)

    Google Scholar 

  105. Colquhoun, H. M., Holton, J., Thompson, D. J., Twigg, M. V.: New Pathways for Organic Synthesis, Plenum Press, New York (1984)

    Google Scholar 

  106. Woodward, R. B., Hoffmann, R.: Angew. Chem. 81, 797 (1969); Angew. Chem. Int. Ed. Engl. 8, 781 (1969)

    Google Scholar 

  107. Benson, S. W.: Thermodynamical Kinetics, Wiley, New York (1976)

    Google Scholar 

  108. Blomquist, A. T., Meinwald, Y. C.: J. Am. Chem. Soc. 81, 667 (1959)

    Google Scholar 

  109. Hall jr., H. K.: J. Org. Chem. 25, 42 (1960)

    Google Scholar 

  110. Williams, J. K., Benson, R. E.: J. Am. Chem. Soc. 84, 1257 (1962)

    Google Scholar 

  111. Cookson, R. C., Gilani, S. S. H., Stevens, I. D. R.: Tetrahedron Lett. 615 (1962)

    Google Scholar 

  112. Cookson, R. C., Dance, J., Hudec, J.: J. Chem. Soc. 5416 (1964)

    Google Scholar 

  113. Heaney, H., Jablonski, J. M.: Tetrahedron Lett. 2733 (1967)

    Google Scholar 

  114. Reppe, W., Schlichting, O., Klager, K., Toepel, T.: Liebigs Ann. Chem. 560, 1 (1948)

    Google Scholar 

  115. Vollhardt, K. P. C.: Angew. Chem. 96, 525 (1984)

    Google Scholar 

  116. Bönnemann, H.: Angew. Chem. 90, 517 (1978): Angew. Chem. Int. Ed. Engl. 17, 505 (1978)

    Google Scholar 

  117. Binger, P., Schroth, G., McMeeking, J.: Angew. Chem. 86, 518 (1974); Angew. Chem. Int. Ed. Engl. 13, 465 (1974)

    Google Scholar 

  118. Krüger, C., Roberts, P. J.: Cryst. Struct. Comm. 3, 459 (1974)

    Google Scholar 

  119. Binger, P., McMeeking, J.: Angew. Chem. 87, 383 (1975); Angew. Chem. Int. Ed. Engl. 14, 371 (1975)

    Google Scholar 

  120. Spielmann, W., Kaufmann, D., de Meijere, A.: Angew. Chem. 90, 470 (1978); Angew. Chem. Int. Ed. Engl. 17, 440 (1978)

    Google Scholar 

  121. Reinhoudt, D. N., Smael, P., van Tilborg, W. J. M., Visser, J. P.: Tetrahedron Lett. 3755 (1973)

    Google Scholar 

  122. van Tilborg, W. J. M., Smael, P., Visser, J. P., Kouwenhoven, C. G., Reinhoudt, D. N.: Recl. Trav. Chim. Pays-Bas 94, 85 (1975)

    Google Scholar 

  123. Noyori, R., Umeda, I., Takya, H.: Tetrahedron Lett. 1189 (1972)

    Google Scholar 

  124. Binger, P., Schuchardt, U.: Angew. Chem. 87, 715 (1975); Angew. Chem. Int. Ed. Engl. 14, 706 (1975)

    Google Scholar 

  125. Older methods are cited in: Rahman, W., Kuivila, H. G.: J. Org. Chem. 31, 772 (1966)

    Google Scholar 

  126. Fisher, F., Applequist, D. E.: J. Org. Chem. 30, 2089 (1965)

    Google Scholar 

  127. Rule, M., Matlin, A. R., Hilinski, E. F., Dougherty, D. A., Berson, J. A.: J. Am. chem. Soc. 101, 5098 (1979)

    Google Scholar 

  128. Billups, W. E., Shields, T. C., Chow, W. Y., Deno, N. C.: J. Org. Chem. 37, 3676 (1972)

    Google Scholar 

  129. Billups, W. E., Chow, W. Y., Leavell, K. H., Lewis, E. S.: J. Org. Chem. 39, 274 (1974)

    Google Scholar 

  130. Osborn, C. L., Shields, T. C., Shoulders, B. A., Krause, J. F., Cortez, H. V., Gardner, P. D.: J. Am. Chem. Soc. 87, 3158 (1965)

    Google Scholar 

  131. Bässler, T.: Dissertation, Universität Saarbrücken (1972)

    Google Scholar 

  132. Makosza, M., Wawrzyniewicz, M.: Tetrahedron Lett. 4659 (1969)

    Google Scholar 

  133. Closs, G. L., Closs, L. E.: J. Am. Chem. Soc. 82, 5723 (1960)

    Google Scholar 

  134. see ref. 28

    Google Scholar 

  135. Thomas, E. W.: Tetrahedron Lett. 24, 1467 (1983)

    Google Scholar 

  136. Sternberg, E., Binger, P.: Tetrahedron Lett. 26, 301 (1985)

    Google Scholar 

  137. Wittig, U., Binger, P.: unpublished results

    Google Scholar 

  138. Schöllkopf, U.: Houben/Weyl 13/1, 167 (1970)

    Google Scholar 

  139. Dunkelblum, E., Brenner, S.: Tetrahedron lett. 669 (1973)

    Google Scholar 

  140. Sisido, K., Utimoto, K.: Tetrahedron Lett. 3267 (1966)

    Google Scholar 

  141. Utimoto, K., Tamura, M., Sisido, K.: Tetrahedron 29, 1169 (1973)

    Google Scholar 

  142. Schweizer, E. E., Berninger, C. J., Thompson, J. G.: J. Org. Chem. 33, 336 (1968)

    Google Scholar 

  143. Trost, B. M., LaRochelle, R., Bogdanowicz, M. J.: Tetrahedron Lett. 3449 (1970)

    Google Scholar 

  144. Huet, F., Lechevallier, A., Conia, J. M.: Tetrahedron Lett. 2521 (1977)

    Google Scholar 

  145. Lechevallier, A., Huet, F., Conia, J. M.: Tetrahedron 39, 3307 (1983)

    Google Scholar 

  146. Osborne, N. F.: J. Chem. Soc. Perkin Trans. I, 1435 (1982)

    Google Scholar 

  147. Hiyama, T., Kanakura, A., Morizawa, Y., Nozaki, H.: Tetrahedron Lett. 23, 1279 (1982)

    Google Scholar 

  148. Hässig, R., Siegel, H., Seebach, D.: Chem. Ber. 115, 1990 (1982)

    Google Scholar 

  149. Halazy, S., Dumont, W., Krief, A.: Tetrahedron Lett. 22, 4737 (1981)

    Google Scholar 

  150. Cohen, T., Sherbine, J. P., Matz, J. R., Hutchins, R. R., McHenry, B. M., Willey, P. R.: J. Am. Chem. Soc. 106, 3245 (1984)

    Google Scholar 

  151. see ref. 106

    Google Scholar 

  152. Battioni, P., Vo-Quang, L., Vo-Quang, Y.: Bull. Soc. Chim. France 3942 (1970)

    Google Scholar 

  153. Dehmlow, E. V.: Chem. Ber. 100, 2779 (1967)

    Google Scholar 

  154. Noyori, R., Takaya, H., Nakanisi, Y., Nozaki, H.: Can. J. Chem. 47, 1242 (1969)

    Google Scholar 

  155. Molchanov, A. P., Noskova, O. V., Kostikov, R. R.: Zh. Org. Khim. 19, 1981 (1983); J. Org. Chem. USSR 19, 1740 (1983)

    Google Scholar 

  156. Creary, X.: J. Org. Chem. 43, 1777 (1978)

    Google Scholar 

  157. Blomquist, A. T., Conolly, D. J.: Chem. Ind. 310 (1962)

    Google Scholar 

  158. Stang, P. J.: Acc. Chem. Res. 15, 348 (1982)

    Google Scholar 

  159. Fox, D. P., Bjork, J. A., Stang, P. J.: J. Org. Chem. 48, 3994 (1983)

    Google Scholar 

  160. Vogel, E.: Angew. Chem. 72, 4 (1960)

    Google Scholar 

  161. Berson, J. A. et al.: J. Am. Chem. Soc. 104, 2233 (1982); ibid. 104, 2228 (1982); ibid. 104, 2223 (1982); ibid. 104, 2217 (1982); ibid. 104, 2209 (1982); ibid. 102, 3870 (1980)

    Google Scholar 

  162. Dixon, D. A., Foster, R., Halgren, T. A., Lipscomb, W. N.: J. Am. Chem. Soc. 100, 1359 (1978)

    Google Scholar 

  163. Hehre, W. J., Salem, L., Willcott, M. R.: J. Am. Chem. Soc. 96, 4328 (1974)

    Google Scholar 

  164. Dewar, M. J. S., Wasson, J. S.: J. Am. Chem. Soc. 93, 3081 (1971)

    Google Scholar 

  165. Aue, D. H., Lorens, R. B., Helwig, G. S.: J. Org. Chem. 44, 1202 (1979)

    Google Scholar 

  166. see ref. 22

    Google Scholar 

  167. Hartmann, W., Heine, H.-G., Hinz, J., Wendisch, D.: Chem. Ber. 110, 2986 (1977)

    Google Scholar 

  168. Noyori, R., Hayashi, N., Kato, M.: Tetrahedron Lett. 2983 (1973)

    Google Scholar 

  169. Noyori, R., Ishigami, T., Hayashi, N., Takaya, H.: J. Am. Chem. Soc. 95, 1674 (1973)

    Google Scholar 

  170. Noyori, R., Kumagai, Y., Umeda, I., Takaya, H.: J. Am. Chem. Soc. 94, 4018 (1972)

    Google Scholar 

  171. Barton, T. J., Rogido, R. J.: Tetrahedron Lett. 3901 (1972)

    Google Scholar 

  172. Laurie, V. W., Stigliani, W. M.: J. Am. Chem. Soc. 92, 1485 (1970)

    Google Scholar 

  173. Krüger, C., Chiang, A.-P.: unpublished results

    Google Scholar 

  174. v.d. Saal, W., Risler, W., Stawitz, J., Quast, H.: J. Org. Chem. 48, 2374 (1983)

    Google Scholar 

  175. Barfield, M., Spear, R. J., Sternhell, S.: Chem. Rev. 76, 593 (1976)

    Google Scholar 

  176. Rol, N. C., Clague, A. D. H.: Org. Magn. Reson. 16, 187 (1981)

    Google Scholar 

  177. Crawford, R. J., Tokunaga, H., Shrijver, L. M. H. C., Godard, J. C., Nakashima, T.: Can. J. Chem. 56, 992 + 998 (1978)

    Google Scholar 

  178. Aue, D. H., Meshishnek, M. J.: J. Am. Chem. Soc. 99, 223 (1977)

    Google Scholar 

  179. Günther, H., Herrig, W.: Chem. Ber. 106, 3938 (1973)

    Google Scholar 

  180. Bertie, J. E., Norton, M. G.: Can. J. Chem. 48, 3889 (1970); ibid. 49, 2229 (1971)

    Google Scholar 

  181. Bertie, J. E., Sunder, S.: ibid. 50, 765 (1972)

    Google Scholar 

  182. Mitchell, R. W., Merritt, J. A.: Spectrochim. Acta 27a, 1609 (1971)

    Google Scholar 

  183. Sieiro, C., Ponce, C.: Ann. Quim. 72, 201 (1976)

    Google Scholar 

  184. Bieri, G., Burger, F., Heilbronner, E., Maier, J. P.: Helv. Chim. Acta 60, 2213 (1977)

    Google Scholar 

  185. Wiberg, K. B., Ellison, G. B., Wendoloski, J. J., Brundle, C. R., Kuebler, N. A.: J. Am. Chem. Soc. 98, 7179 (1976)

    Google Scholar 

  186. Wiberg, K. B. et al.: J. Am. Chem. Soc. 105, 3638 (1983); ibid. 104, 5239 (1982); ibid. 104, 2056 (1982)

    Google Scholar 

  187. Stirling, C. J. M.: Pure and Appl. Chem. 56, 1781 (1984)

    Google Scholar 

  188. for a review see: Gajewski, J. J.: Hydrocarbon Thermal Rearrangements, Academic Press, New York (1981)

    Google Scholar 

  189. Chesick, J. P.: J. Am. Chem. Soc. 85, 2720 (1963)

    Google Scholar 

  190. Gajewski, J. J.: ibid. 90, 7178 (1968)

    Google Scholar 

  191. Gilbert, J. C., Butler, J. R.: ibid. 92, 2168 (1970)

    Google Scholar 

  192. von E. Doering, W., Roth, H. D.: Tetrahedron 26, 2825 (1970)

    Google Scholar 

  193. Dewar, M. J. S., Wasson, J. S.: J. Am. Chem. Soc. 93, 3081 (1971)

    Google Scholar 

  194. Yarkony, D. R., Schaefer III, H. F.: J. Am. Chem. Soc. 96, 3754 (1974)

    Google Scholar 

  195. Borden, W. T.: ibid. 97, 2906 (1975)

    Google Scholar 

  196. Davis, J. H., Goddard III, W. A.: ibid. 98, 303 (1976)

    Google Scholar 

  197. Dowd, P., Chow, M.: Tetrahedron 38, 799 (1982)

    Google Scholar 

  198. Salaün, J. R., Conia, J. M.: J. Chem. Soc. Chem. Commun. 1579 (1971)

    Google Scholar 

  199. Crandall, J. K., Conover, W. W.: J. Org. Chem. 43, 3533 (1978); here further literature

    Google Scholar 

  200. Köster, R., Arora, S., Binger, P.: Liebigs Ann. Chem. 1619 (1973)

    Google Scholar 

  201. Binger, P.: Angew. Chem. 84, 483 (1972); Angew. Chem. Int. Ed. Engl. 11, 433 (1972)

    Google Scholar 

  202. Bartlett, P. D., Wheland, R. C.: J. Am. Chem. Soc. 94, 2145 (1972)

    Google Scholar 

  203. Noyori, R., Hayashi, N., Kato, M.: J. Am. Chem. Soc. 93, 4948 (1971)

    Google Scholar 

  204. Kaufmann, D., de Meijere, A.: Angew. Chem. 85, 151 (1973); Angew. Chem. Int. Ed. Engl. 12, 159 (1973)

    Google Scholar 

  205. M=Fe: Whitesides, T. H., Slaven, R. W.: J. Organomet. Chem. 67, 99 (1974)

    Google Scholar 

  206. M=Fe: Whitesides, T. H., Slaven, R. W., Calabrese, J. C.: Inorg. Chem. 13, 1895 (1974)

    Google Scholar 

  207. M=Fe: Green, M., Howard, J. A. K., Hughes, R. P., Kellett, S. C., Woodward, P.: J. Chem. Soc. Dalton Trans. 2007 (1975)

    Google Scholar 

  208. M=Fe: Pinhas, A. R., Samuelson, A. G., Risemberg, R., Arnold, E. V., Clardy, J., Carpenter, B. K.: J. Am. Chem. Soc. 103, 1668 (1981)

    Google Scholar 

  209. M=Ni: Englert, M., Jolly, P. W., Wilke, G.: Angew. Chem. 83, 84 (1971); Angew. Chem. Int. Ed. Engl. 10, 77 (1971)

    Google Scholar 

  210. M=Ni: Binger, P., Doyle, M. J., Benn, R.: Chem. Ber. 116, 1 (1983)

    Google Scholar 

  211. M=Ni: Isaeva, L. S., Peganova, T. A., Petrovskii, P. V., Furmann, D. B., Zotova, S. V., Kudryashev, A. V., Bragin, O. V.: J. Organomet. Chem. 258, 367 (1983)

    Google Scholar 

  212. M=Pd: Green, M., Hughes, R. P.: J. Chem. Soc. Dalton Trans. 1880 (1976)

    Google Scholar 

  213. M=Pd: Büch, H. M.: Dissertation, Universität Kaiserslautern (1982)

    Google Scholar 

  214. M=Fe: see ref. 147a, 147d

    Google Scholar 

  215. M=Ni: see ref. 148a

    Google Scholar 

  216. M=Pd: see ref. 149a

    Google Scholar 

  217. M=Fe: Chisnall, B. M., Green, M., Hughes, R. P., Welch, A. J.: J. Chem. Soc. Dalton Trans. 1899 (1976)

    Google Scholar 

  218. M=Fe: see ref. 147d

    Google Scholar 

  219. M=Fe: Noyori, R., Nishimura, T., Takaya, H.: Chem. Commun. 89 (1969)

    Google Scholar 

  220. M=Fe: see ref. 147a

    Google Scholar 

  221. M=Fe: Pinhas, A. R., Carpenter, B. K.: J. Chem. Soc. Chem. Commun. 17 (1980); ibid. 15 (1980)

    Google Scholar 

  222. M=Mo: Barnes, S. G., Green, M.: J. Chem. Soc. Chem. Commun. 267 (1980)

    Google Scholar 

  223. M=Mo: Allen, S. R., Barnes, S. G., Green, M., Moran, G., Trollope, L., Murrall, N. W., Welch, A. J., Sharaiha, D. M.: J. Chem. Soc. Dalton Trans. 1157 (1984)

    Google Scholar 

  224. M=Pd: Noyori, R., Takaya, H.: Chem. Commun. 525 (1969)

    Google Scholar 

  225. M=Pd: Albright, T. A., Clemens, P. A., Hughes, R. P., Hunton, D. E., Margerum, L. D.: J. Am. Chem. Soc. 104, 5369 (1982)

    Google Scholar 

  226. M=Rh; Ir: see ref. 147c

    Google Scholar 

  227. M=Co: Binger, P., Martin, T. R., Benn, R., Rufinska, A., Schroth, G.: Z. Naturforsch. 39b, 993 (1984)

    Google Scholar 

  228. M=Co: see ref. 156b

    Google Scholar 

  229. M=Ni: see ref. 148b

    Google Scholar 

  230. M=Ni: see ref. 149b

    Google Scholar 

  231. Seebach, D.: Houben/Weyl 4/4, 1 (1971)

    Google Scholar 

  232. Corey, E. J., Mitra, R. B., Uda, H.: J. Am. Chem. Soc. 85, 362 (1963); ibid. 86, 485 (1964)

    Google Scholar 

  233. see ref. 92

    Google Scholar 

  234. Baldwin, S. W.: Organic Photochem. 5, 123 (1981)

    Google Scholar 

  235. Chapman, O. L., Weiss, D. S.: ibid. 3, 197 (1973)

    Google Scholar 

  236. de Mayo, P.: Acc. Chem. Res. 4, 41 (1971)

    Google Scholar 

  237. Bauslaugh, P. G.: Synthesis 287 (1970)

    Google Scholar 

  238. Eaton, P. E.: Acc. Chem. Res. 1, 50 (1968)

    Google Scholar 

  239. Chapman, O. L., Lenz, G.: Organic Photochem. 1, 283 (1967)

    Google Scholar 

  240. Mango, F. D., Schachtschneider, J. H.: J. Am. Chem. Soc. 89, 2484 (1967)

    Google Scholar 

  241. Mango, F. D.: Coord. Chem. Rev. 15, 109 (1975)

    Google Scholar 

  242. Heimbach, P.: Angew. Chem. 82, 550 (1970); Angew. Chem. Int. Ed. Engl. 9, 528 (1970)

    Google Scholar 

  243. Bishop III, K. C.: Chem. Rev. 76, 461 (1976)

    Google Scholar 

  244. Wilke, G.: J. Organomet. Chem. 200, 349 (1980)

    Google Scholar 

  245. Puddephatt, R. J.: Comments Inorg. Chem. 2, 69 (1982)

    Google Scholar 

  246. Stockis, A., Hoffmann, R.: J. Am. Chem. Soc. 102, 2952 (1980)

    Google Scholar 

  247. McKinney, R. J., Thorn, D. L., Hoffmann, R., Stockis, A.: J. Am. Chem. Soc. 103, 2595 (1981)

    Google Scholar 

  248. Binger, P.: Angew. Chem. 84, 352 (1972); Angew. Chem. Int. Ed. Engl. 11, 309 (1972)

    Google Scholar 

  249. Binger, P.: Synthesis 427 (1973)

    Google Scholar 

  250. Binger, P.: unpublished results, see Habilitationsschrift, Universität Kaiserslautern (1982)

    Google Scholar 

  251. Noyori, R., Ishigami, T., Hayashi, N., Takaya, H.: J. Am. Chem. Soc. 95, 1674 (1973)

    Google Scholar 

  252. Kaufmann, D., de Meijere, A.: Chem. Ber. 117, 3134 (1984)

    Google Scholar 

  253. Binger, P., Brinkmann, A., Wedemann, P.: Chem. Ber. 116, 2920 (1983)

    Google Scholar 

  254. Wassermann, A.: Diels-Alder Reactions, Elsevier, New York (1965)

    Google Scholar 

  255. Wollweber, H.: Houben/Weyl 5/Ic, 977 (1970); Diels-Alder Reaktion, Thieme-Verlag, Stuttgart (1972)

    Google Scholar 

  256. Sauer, J., Sustmann, R.: Angew. Chem. 92, 773 (1980); Angew. Chem. Int. Ed. Engl. 19, 779 (1980)

    Google Scholar 

  257. Petrzilka, M., Grayson, J. I.: Synthesis 753 (1981)

    Google Scholar 

  258. House, H. O.: Modern Synthetic Reactions, 2nd ed., p. 606–611, 621–623, Benjamin, New York (1972)

    Google Scholar 

  259. Jung, M. E.: Tetrahedron 32, 3 (1976)

    Google Scholar 

  260. Gawley, R. E.: Synthesis 777 (1976)

    Google Scholar 

  261. Paquette, L. A. et al.: Recent Developments in Polycyclopentanoid Chemistry, Tetrahedron Symposia-in-Print 37, 4357 (1981)

    Google Scholar 

  262. Trost, B. M.: Cyclopentanoids: A Challenge for New Methodology, Chem. Soc. Rev. 11, 141 (1982)

    Google Scholar 

  263. Harre, M., Raddatz, P., Walenta, R., Winterfeldt, E.: Angew. Chem. 94, 496 (1982); Angew. Chem. Int. Ed. Engl. 21, 480 (1982)

    Google Scholar 

  264. Ramaiah, M.: Synthesis 529 (1984)

    Google Scholar 

  265. Paquette, L. A.: Top. Curr. Chem. 119, 1 (1984)

    Google Scholar 

  266. for an excellent review see: Tietze, L.-F.: Angew. Chem. 95, 840 (1983); Angew. Chem. Int. Ed. Engl. 22, 828 (1983)

    Google Scholar 

  267. for a recent synthesis of loganin aglucon via cycloaddition methodology see: Trost, B. M., Nanninga, T. N.: J. Am. Chem. Soc. 107, 1293 (1985)

    Google Scholar 

  268. Paquette, L. A., Ternansky, R. J., Balogh, D. W., Kentgen, G.: J. Am. Chem. Soc. 105, 5446 (1983)

    Google Scholar 

  269. Dowd, P.: Acc. Chem. Res. 5, 242 (1972)

    Google Scholar 

  270. Berson, J. A.: ibid. 11, 446 (1978)

    Google Scholar 

  271. some specific intramolecular examples are known, e.g.: Little, R. D., Muller, G. W., Venegas, M. G., Caroll, G. L., Bukhari, A., Patton, L., Stone, K.: Tetrahedron 37, 4371 (1981)

    Google Scholar 

  272. Trost, B. M., Chan, D. M. T.: J. Am. Chem. Soc. 105, 2315 and 2326 (1983)

    Google Scholar 

  273. Trost, B. M., Nanninga, T. N., Satoh, T.: J. Am. Chem. Soc. 107, 721 (1985)

    Google Scholar 

  274. Trost, B. M., Nanninga, T. N.: ibid. 107, 1075 (1985)

    Google Scholar 

  275. Shimizu, I., Ohashi, Y., Tsuji, J.: Tetrahedron Lett. 25, 5183 (1984)

    Google Scholar 

  276. Kiji, J., Masui, K., Furukawa, J.: Bull. Chem. Soc. Jap. 44, 1956 (1971)

    Google Scholar 

  277. Noyori, R., Odagi, T., Takaya, H.: J. Am. Chem. Soc. 92, 5780 (1970)

    Google Scholar 

  278. Noyori, R., Kumagai, Y., Umeda, I., Takaya, H.: J. Am. Chem. Soc. 94, 4018 (1972)

    Google Scholar 

  279. Noyori, R., Yamakawa, M., Takaya, H.: Tetrahedron Lett. 4823 (1978)

    Google Scholar 

  280. Binger, P., Brinkmann, A., Richter, W. J.: Tetrahedron Lett. 24, 3599 (1983)

    Google Scholar 

  281. Binger, P., Wedemann, P.: Tetrahedron Lett. 26, 1045 (1985)

    Google Scholar 

  282. Ukai, T., Kawazura, H., Ishii, Y., Bonnet, J. J., Ibers, J. A.: J. Organomet. Chem. 65, 253 (1974)

    Google Scholar 

  283. Tatsuno, Y., Yoshida, T., Otsuka, S.: Inorg. Synth. 19, 220 (1979)

    Google Scholar 

  284. Kühn, A., Werner, H.: J. Organomet. Chem. 179, 421 (1979)

    Google Scholar 

  285. Binger, P., Schuchardt, U.: Chem. Ber. 114, 3313 (1981)

    Google Scholar 

  286. Chen, S., Binger, P.: unpublished results

    Google Scholar 

  287. Binger, P., Brinkmann, A.: unpublished results

    Google Scholar 

  288. Balavoine, G., Eskenazi, C., Guillemot, M.: J. Chem. Soc. Chem. Commun. 1109 (1979)

    Google Scholar 

  289. Trost, B. M., Renaut, P.: J. Am. Chem. Soc. 104, 6668 (1982)

    Google Scholar 

  290. Binger, P., Schuchardt, U.: Chem. Ber. 113, 3334 (1980)

    Google Scholar 

  291. Binger, P., Schuchardt, U.: Chem. Ber. 113, 1063 (1980)

    Google Scholar 

  292. Binger, P., Bentz, P.: Angew. Chem. 94, 636 (1982); Angew. Chem. Int. Ed. Engl. 21, 622 (1982); Angew. Chem. Suppl. 1385–1391 (1982)

    Google Scholar 

  293. Trost, B. M.: Fundamental Research in Homogenous Catalysis, 4, 117, Plenum Press (1984)

    Google Scholar 

  294. Only in the case of 2,3-di-(or higher) alkylated methylenecyclopropanes, in which the distal C-C bond is strengthened, proximal ring-opening is observed, leading to 1,3-butadienes or 1,4-pentadienes. In addition, methylenecyclopropanes with an alkyl substituent larger than methyl in the 2-position are mostly isomerized to 1,3-butadienes despite of distal cleavage reflecting the fact that elimination is faster than cycloaddition.

    Google Scholar 

  295. Binger, P., Bentz, P.: J. Organomet. Chem. 221, C33 (1981)

    Google Scholar 

  296. Binger, P., Wedemann, P.: Tetrahedron Lett. 24, 5847 (1983)

    Google Scholar 

  297. Jolly, P. W., Wilke, G.: The Organic Chemistry of Nickel, Vol. II, Academic Press, New York (1975)

    Google Scholar 

  298. Jolly, P. W.: Comprehensive Organometallic Chemistry, Vol. 8, p. 649, Pergamon Press (1982)

    Google Scholar 

  299. Keim, W., Behr, A., Röper, M.: ibid. p. 371

    Google Scholar 

  300. Binger, P., Lü, Q.-H., Wedemann, P.: Angew. Chem. 97, 333 (1985); Angew. Chem. Int. Ed. Engl. 24, 316 (1985)

    Google Scholar 

  301. Eisenberg, R., Hendriksen, D. E.: Adv. Catal. 28, 79 (1979)

    Google Scholar 

  302. For an excellent review of metal catalyzed CO2-reactions see: Sneedon, R. P. A.: Comprehensive Organometallic Chemistry, Vol. 8, p. 225, Pergamon Press (1982)

    Google Scholar 

  303. Hoberg, H., Oster, B. W.: Synthesis 324 (1982)

    Google Scholar 

  304. Hoberg, H., Burkhart, G.: Synthesis 525 (1979)

    Google Scholar 

  305. Inoue, Y., Itoh, Y., Hashimoto, H.: Chem. Lett. 633 (1978)

    Google Scholar 

  306. Ohno, K., Mitsuyasu, T., Tsuji, J.: Tetrahedron 28, 3705 (1972)

    Google Scholar 

  307. Sasaki, Y., Inoue, Y., Hashimoto, H.: J. Chem. Soc. Chem. Commun. 605 (1976)

    Google Scholar 

  308. Musco, A.: J. Chem. Soc. Perkin Trans. I, 693 (1980)

    Google Scholar 

  309. Jolly, P. W.: Comprehensive Organometallic Chemistry, Vol. 8, 671, Pergamon Press (1982)

    Google Scholar 

  310. Maurin, R., Bertrand, M.: Bull. Soc. Chim. France, 3, 998 (1970)

    Google Scholar 

  311. Isaacs, N. S., Stanbury, P.: J. Chem. Soc. Perkin Trans., 166 (1973)

    Google Scholar 

  312. Weintz, H. J.: Dissertation, University Kaiserslautern (1984)

    Google Scholar 

  313. Weintz, H. J., Binger, P.: Tetrahedron Lett. 26, 4075 (1985)

    Google Scholar 

  314. Binger, P., Weintz, H. J.: Chem. Ber., 117, 654 (1984)

    Google Scholar 

  315. Inoue, Y., Hibi, T., Satake, M., Hashimoto, H.: J. Chem. Soc. Chem. Commun., 982 (1979)

    Google Scholar 

  316. Inoue, Y., Hibi, T., Kawashima, Y., Hashimoto, H.: Chem. Lett. 1521 (1980)

    Google Scholar 

  317. Binger, P., Brinkman, A., McMeeking, J.: Liebigs Ann. Chem. 1065 (1977)

    Google Scholar 

  318. Sternberg, E., Binger, P.: unpublished results

    Google Scholar 

  319. Trost, B. M., Nanninga, T. N., Chan, D. M.: Organometallics 1, 1543 (1982)

    Google Scholar 

  320. Büch, H. M., Schroth, G., Mynott, R., Binger, P.: J. Organomet. Chem. 247, C63 (1983)

    Google Scholar 

  321. Albright, T. A.: J. Organomet. Chem. 198, 159 (1980)

    Google Scholar 

  322. Gordon, D. J., Fenske, R. F., Nanninga, T. N., Trost, B. M.: J. Am. Chem. Soc. 103, 5974 (1981)

    Google Scholar 

  323. Knapp, S., O'Connor, U., Nobilio, D.: Tetrahedron Lett. 21, 4557 (1980)

    Google Scholar 

  324. Magnus, P., Ruagliato, D. A.: Organometallics 1, 1243 (1982)

    Google Scholar 

  325. Piers, E., Kasunaratne, V.: J. Chem. Soc. Chem. Commun. 935 (1983)

    Google Scholar 

  326. Piers, E., Kasunaratne, V.: J. Chem. Soc. Chem. Commun. 959 (1983)

    Google Scholar 

  327. Bentz, P.: Dissertation, University Kaiserslautern 1982

    Google Scholar 

  328. Shortridge, R. W., Craig, R. A., Greenlee, K. W., Derfer, J. M., Boord, C. E.: J. Am. Chem. Soc. 70, 946 (1948)

    Google Scholar 

  329. v. R. Schleyer, P.: Chem. Commun. 569 (1968)

    Google Scholar 

  330. Nametkin, N. S., Ydovin, V. M., Finkel'shtein, E. Sh., Propov, A. M., Egorow, A. V., Ivz. Akad. Nauk, SSSR, Ser. Khim. 2806 (1973); Engl. Transl. 2742 (1973)

    Google Scholar 

  331. Noyce, D. S., Fessendes, J. S.: J. Org. Chem. 24, 715 (1959)

    Google Scholar 

  332. Hall jr., H. K.: Macromolecules 4, 139 (1971)

    Google Scholar 

  333. Dolby, L. J., Esfandiori, S., Ellings, C. A., Marshall, K. S.: J. Org. Chem. 36, 1277 (1971)

    Google Scholar 

  334. Kurosawa, K., Obara, M.: Bull. Chem. Soc. Jap. 39, 52 (1966)

    Google Scholar 

  335. Bartlett, P. A., Green III, F. R.: J. Am. Chem. Soc. 100, 4858 (1978)

    Google Scholar 

  336. Guiliano, R., Artico, M., Nacci, V.: Ann. Chim. (Roma) 51, 491 (1961); C.A. 63, 5066 (1965)

    Google Scholar 

  337. Auwers, K.: Ber. Dtsch. Chem. Ges. 26, 364 (1893)

    Google Scholar 

  338. Honda, M., Hirata, K., Sukoca, H., Hatsuki, T., Yamaguchi, M.: Tetrahedron Lett. 22, 2679 (1981)

    Google Scholar 

  339. Sakai, K. I. J., Oda, O.: Tetrahedron Lett. 3021 (1975)

    Google Scholar 

  340. Oda, O., Kojima, K., Sakai, K.: Tetrahedron Lett. 3709 (1975)

    Google Scholar 

  341. Goldsmith, D. J., Thottathil, J. K.: Tetrahedron Lett. 22, 2447 (1981)

    Google Scholar 

  342. Boeckman jr., R. K., Nagely, P. C., Arthur, S. D.: J. Org. Chem. 45, 752 (1980)

    Google Scholar 

  343. Trost, B. M., Renaut, P.: J. Am. Chem. Soc. 104, 6668 (1982)

    Google Scholar 

  344. Sternberg, E., Binger, P.: unpublished

    Google Scholar 

  345. Trost, B. M., Nanninga, T. N.: J. Am. Chem. Soc. 107, 1293 (1985)

    Google Scholar 

  346. Trost, B. M., Chan, D. M. T.: J. Am. Chem. Soc. 103, 5972 (1981)

    Google Scholar 

  347. Kon, K., Isoe, S.: Tetrahedron Lett. 21, 3399 (1980)

    Google Scholar 

  348. Baker, R., Keen, R. B.: J. Organomet. Chem. 285, 419 (1985)

    Google Scholar 

Download references

Author information

Author notes

  1. Holger Michael Büch

    Present address: Farbwerke Hoechst AG, D-6230, Frankfurt/Main 80

Authors and Affiliations

  1. Max-Planck-Institut für Kohlenforschung, Postfach 101353, D-4330, Mülheim a. d. Ruhr, West Germany (FRG)

    Paul Binger & Holger Michael Büch

Authors
  1. Paul Binger
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Holger Michael Büch
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

A. de Meijere

Rights and permissions

Reprints and permissions

Copyright information

© 1987 Springer-Verlag

About this paper

Cite this paper

Binger, P., Büch, H.M. (1987). Cyclopropenes and methylenecylopropanes as multifunctional reagents in transition metal catalyzed reactions. In: de Meijere, A. (eds) Small Ring Compounds in Organic Synthesis II. Topics in Current Chemistry, vol 135. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-16662-9_4

Download citation

  • DOI: https://doi.org/10.1007/3-540-16662-9_4

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-16662-7

  • Online ISBN: 978-3-540-39846-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation