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Synthesis 1995; 1995(8): 969-972
DOI: 10.1055/s-1995-4025
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Cyclic 2-Ynones from Cyclic Alkynes via Ring Enlargement

Rolf Gleiter* , Martin Merger
  • *Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany, Fax +49(6221)564205
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Publication Date:
31 December 2000 (online)

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The reaction of alkynes with trichloromethane/butyllithium in tetrahydrofuran at -78°C followed by hydrolysis yields 2-ynones and cyclopropenones. This has been demonstrated for dec-5-yne, cyclooctyne, cyclodeca-1,6-diyne, cyclododeca-1,7-diyne, and cyclotetradeca-1,8-diyne. Cyclooctyne yields cyclonon-2-ynone for the first time, which proves the aptitude of this method even for the synthesis of strained cyclic 2-ynones. With the cycloalkadiynes almost only monofunctional transformation to diynes and bicycloalkenynones was observed.

cyclic 2-ynones - cyclic diynones - CO insertion alkynes - dichlorocyclopropenation alkynes - trichloromethyllithium

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