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Formation of δ-Sultines (1,2-Oxathiane 2-Oxides) from Thiolane 1-Oxides

✍ Scribed by Barbara Schuler; Jürgen Voss

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
258 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

2-(Alkylthio)-2-benzylthiolane 1-oxides (1a, b) and 2-esters (δ-sultines) 2 are formed. Only (1R*,2S*)-1b is reactive whereas (1R*,2R*)-1b is not attacked. This observation is (alkylthio)-2-(α-hydroxybenzyl)thiolane 1-oxides (1c, d) are oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA). explained with the formation of a cyclic intermediate 3.

Under ring enlargement the corresponding cyclic sulfinate

[ ] Part 7: Ref. [4] [a] Institut für Organische Chemie der Universität Hamburg, To achieve a reaction with (1R*,2R*)-1b as well as with

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