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One‐Pot Preparation of C 1 ‐Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal‐Cyanide‐Free Conditions
Author(s) -
Ezawa Masatoshi,
Togo Hideo
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700277
Subject(s) - chemistry , wittig reaction , cyanide , ylide , organic chemistry , hydrolysis , nitrile , alcohol
A one‐pot protocol to obtain C 1 ‐homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with p TsOH (Ts = para ‐toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl‐type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.