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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