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Reaction of benzhydrol with urea and thiourea

✍ Scribed by Aziz-Ur Rahman; Rama Kant Singh


Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
272 KB
Volume
78
Category
Article
ISSN
0165-0513

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✦ Synopsis


Abstract

The reaction between benzhydrol and urea resulting in the formation of N,N′‐bis(diphenylmethyl)urea and bis(diphenylmethyl) ether, has been studied with a view to substantiate the reaction mechanism suggested by Rahman and Farooq^1^ for the formation of the former in a reaction between benzilic acid and urea, based on decarboxylation of benzilic acid.

The reaction mechanism postulated by Dannenberg and Rahman^2^ for the formation of N,N′‐bis(diphenylmethyl) thiourea (III), bis(diphenylmethyl) disulphide (IV) and bis(diphenylmethyl) sulphide (V) in a reaction between benzilic acid and thiourea, based mainly on initial benzhydrylation (diphenylmethylation) of thiourea to yield N‐(diphenylmethyl) thiourea (VIII) and also S‐(diphenylmethyl)‐isothiourea (VII), which undergo appropriate changes to yield eventually III, IV and V, has been substantiated by the identity of the products of reaction between benzhydrol and thiourea, with III, IV and V. Further confirmation of the mechanism is afforded by the isolation of a small amount of VII from the reaction product of benzhydrol and thiourea. The comparative mechanisms of the reaction between benzilic acid and thiourea on the one hand and of that between benzhydrol i.e. β€˜decarboxylated benzilic acid’ and thiourea, on the other, are discussed.


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## Abstract Title epoxide (I) reacts with thiourea both in protic and aprotic solvents to furnish predominantly the unexpected product (III) generated by an intramolecular β€œhaloform” decomposition.