Issue 18, 1994
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Chemical transformations of 2,7-di-tert-butylthiepine

Shoko Yamazaki,   Akira Isokawa,   Kagetoshi Yamamoto  and  Ichiro Murata  

Abstract

Selected chemical transformations of a monocyclic thiepine 2,7-di-tert-butylthiepine 1 have been examined. Oxidation of the thiepine 1 gave the unstable thiepine 1-oxide 3, although further oxidation to form the thiepine 1,1-dioxide 4 did not proceed whilst S-methylation with methyl iodide–silver tetrafluoroborate gave rearranged aromatized compounds. In these electrophilic reactions at sulfur, the steric repulsion by two tert-butyl groups possibly causes the formation of the endo-sulfur coordinated species. Bromination gave either the ring-contracted thiophene 12, or the thiopyran 17, depending on the reaction conditions. The cycloaddition with tetracyanoethylene (TCNE) gave the [4 + 2] adduct 22.

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Article information

DOI
https://doi.org/10.1039/P19940002631
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 2631-2635

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Chemical transformations of 2,7-di-tert-butylthiepine

S. Yamazaki, A. Isokawa, K. Yamamoto and I. Murata, J. Chem. Soc., Perkin Trans. 1, 1994, 2631 DOI: 10.1039/P19940002631

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