Studies in claisen rearrangement - novel thermal and mercuric trifluroacetate induced transformations of 2,4-di(N-aryl)amino-1,3,5-triazin-6yl-prop-2-y

Bindu Madhavan, G. V. ; Balasubramanian, K. K. (1985) Studies in claisen rearrangement - novel thermal and mercuric trifluroacetate induced transformations of 2,4-di(N-aryl)amino-1,3,5-triazin-6yl-prop-2-y Tetrahedron, 41 (1). pp. 111-120. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)83475-X

Abstract

The thermal rearrangement of 2,4-di(N-aryl)amino-1,3,5-triazin-6yl-prop-2-ynyl ethers 1̲ yield a mixture of 6-methyleneimidazo(1,2-a)-1,3,5-triazine-4-one 6̲ and 6-methylimidazo(1,2-a)-1,3,5-triazine-4-one 7̲, whereas under the influence of mercuric trifluroacetate the ethers 1̲ yield only 6̲, at room temperature. Mechanisms invoking [3,3] sigmatropic rearrangement of ethers 1̲ were proposed to account for the product formation.

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