Aroylation of carbanions derived from N-(diphenylmethyl)arylmethanimines. A synthesis of 4-aroyloxy-2-azabuta-1,3-dienes
Abstract
The acylation of carbanions derived from N-(diphenylmethyl)arylmethanimines using aroyl chlorides, allows the preparation of a new type of substituted 2-azabuta-1,3-dienes in which the imino group is conjugated with an enol ester. The reaction is quite general and facilitates the preparation of a wide range of 2-azadienes with electron-donating and electron-withdrawing groups on the phenyl rings. The site selectivity for the attack of the electrophile on the aza-allyl anion can be controlled by the substituents on the carbanion and on the hardness of the electrophile.
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