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Synthesis of β,γ-unsaturated phenyl esters by aluminium chloride initiated reactions of allylsilanes with aryl chloroformates

✍ Scribed by Mayr, Herbert ;Gabriel, Andreas O. ;Schumacher, Ralf

Book ID: 102367385
Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 471 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1995199509220

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✦ Synopsis

Abstract

Phenyl chloroformate (1) reacts with the allylsilanes 2a–h in the presence of aluminium chloride to give the β,γ‐unsaturated phenyl esters 3a–h in 50–90% yield. While these reactions proceed in the usual manner with allylic inversion, (1,1‐dimethylallyl)trimethylsilane (2i) reacts with allyl retention to yield the 2,2‐dimethyl‐3‐butenoate 3i. Attempts to use 1 for the phenoxycarbonylation of arenes were not successful.

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