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Chirality in unsymmetrically substituted benzopentathiepins: The result of a high barrier to ring inversion

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
39
Identifiers
DOI: 10.1016/0040-4039(94)85356-8

Abstract

Abstract The 1H NMR spectrum of varacin ( 1), the first naturally-occurring compound determined to bear a 1,2,3,4,5-benzopentathiepin ring, shows unexpectedly complex signals for the side chain methylene protons. Evidence is presented which indicates that unsymmetrically substituted benzopentathiepins are asymmetric molecules as a result of a high energy barrier to inversion of the low energy chair conformations of the polysulfide ring. Derivatization of varacin with a chiral auxiliary provides diastereomeric products which can be separated by fractional recrystallization.

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