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Preparation of α-substituted S-phenylthio esters from 2-nitro-2-phenylthio oxiranes

✍ Scribed by Mark Ashwell; Richard F.W. Jackson; Joanna M. Kirk

Book ID: 104204581
Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 1021 KB
Volume: 46
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89058-x

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✦ Synopsis

2-Nitro-2-phenylthio oniranes (3), prepared by nucleophilic epoxidation of I-nitro-I-phenyllhio alkenes (I), react with a v&y of heteroatomic nucleophiles to give a-substituted S-phenylthio esters (2). Of special note is the efficient reaction of 2-n&o-2-phenylthio oxiranes with boron trifruOride etherate in toluene at room temperature to give a-fluoro S-phenylthio esters (8).

SPh PhS&02 + PhS&Oz

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