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The intramolecular sila-Pummerer cyclization: A new route to sulfur heterocycles

✍ Scribed by Ian W. J. Still; F. Dean Toste

Book ID: 102846598
Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 713 KB
Volume: 5
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520050310

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✦ Synopsis

The generality of the intramolecular cyclization of suitable nucleophilic sites to a -S+=CH2 center created by a sila-Pummerer rearrangement has been investigated. Successful nucleophilic sites included the OH group (in alcohols, carboxylic acids, and hydroxylamines) and the N H group (in amines and carbamates): attempts to produce carbon-based nucleophilic sites were not effective. Successful cyclizations were achieved to produce sulfur heterocycles with 5-, 6-, and 7-membered rings.

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