Effects of ultrasound on the formation of α-benzoylbenzyl cyanide from benzyl cyanide and alkylphenyl ketone from α-alkylbenzyl cyanide by potassium superoxide in the presence of crown ether

Ultrasound accelerates the formation of α-benzoylbenzyl cyanide and benzoic acid in the reaction of benzyl cyanide with potassium superoxide in the presence of 18-crown-6. Similarly, 4-methylbenzyl cyanide, 4-methoxybenzyl cyanide and 4-chlorobenzyl cyanide gave the corresponding α-(4-methylbenzoyl)...

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Bibliographic Details
Published in:	Ultrasonics sonochemistry Vol. 6; no. 1; pp. 105 - 109
Main Authors:	Yim, E.S., Park, M.K., Han, B.H.
Format:	Journal Article
Language:	English
Published:	Netherlands Elsevier B.V 01-03-1999
Subjects:	Benzyl cyanide Crown ether Phenylalkyl ketones Potassium superoxide Sonochemical reaction α-Benzoylbenzyl cyanide Sonochemical reaction Crown ether Phenylalkyl ketones Potassium superoxide α-Benzoylbenzyl cyanide Benzyl cyanide
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Summary:	Ultrasound accelerates the formation of α-benzoylbenzyl cyanide and benzoic acid in the reaction of benzyl cyanide with potassium superoxide in the presence of 18-crown-6. Similarly, 4-methylbenzyl cyanide, 4-methoxybenzyl cyanide and 4-chlorobenzyl cyanide gave the corresponding α-(4-methylbenzoyl)-4-methylbenzyl cyanide, α-(4-methoxybenzoyl)-4-methoxybenzyl cyanide and α-(4-chlorobenzoyl)-4-chlorobenzyl cyanide in 25–43% isolated yields under the same reaction conditions. Benzoic, p-toluic, 4-methoxybenzoic and 4-chlorobenzoic acids were also formed in these reactions. No reaction was observed when the mixture was simply stirred. Reflux instead of sonication gave lower yields of the products. However, α-alkylbenzyl cyanide produced a high yield of the phenylalkyl ketones when stirred. Interestingly, the corresponding benzoic acid was not formed in these reactions. Possible mechanisms for the formation of α-benzoylbenzyl cyanide from benzyl cyanide and phenylalkyl ketones from α-alkylbenzyl cyanide are also proposed.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1350-4177 1873-2828
DOI:	10.1016/S1350-4177(98)00036-4