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Formation of δ‐Sultines (1,2‐Oxathiane 2‐Oxides) from Thiolane 1‐Oxides
Author(s) -
Schuler Barbara,
Voss Jürgen
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199904)1999:4<943::aid-ejoc943>3.0.co;2-f
Subject(s) - chemistry , benzene , ring (chemistry) , medicinal chemistry , organic chemistry
2‐(Alkylthio)‐2‐benzylthiolane 1‐oxides ( 1a , b ) and 2‐(alkylthio)‐2‐(α‐hydroxybenzyl)thiolane 1‐oxides ( 1c , d ) are oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Under ring enlargement the corresponding cyclic sulfinate esters (δ‐sultines) 2 are formed. Only (1 R *,2 S *)‐ 1b is reactive whereas (1 R *,2 R *)‐ 1b is not attacked. This observation is explained with the formation of a cyclic intermediate 3 .