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Intermediacy of α-chloro amides in the basic hydrolysis of α-chloro nitriles to ketones

✍ Scribed by Christopher S. Shiner; Allison M. Fisher; Fred Yacoby

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 285 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94173-x

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✦ Synopsis

Isolable cl-chloro amides are intermediates in the formation of ketones by basic hydrolysis of cl-chloro nitriles. Possible mechanisms for the generation of ketones from cr-chloro amides are discussed. The formation of ketones by basic hydrolysis of cl-chloro nitriles is well known in connection with the use of Z-chloroacrylonitrile as a Diels-Alder ketene equivalent.' This methodology generates formal [4+2] ketene cycloadducts of 1,3-dienes via Diels-Alder

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