Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIV. Reaction of some 3,5-dimethyl-1,4-benzoquinone monoimines with alcohols

Author： Avdeenko A.   Konovalova S.   Vasil’eva V.   Palamarchuk G.   Baumer V.   Shishkin O.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.49, Iss.1, 2013-01, pp. : 49-59

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Abstract

Steric strain in the C=N-C fragment in 3,5-disubstituted N-acyl-1,4-benzoquinone monoimines, unlike their N-arylsulfonyl analogs, leads to increase of the C=N-C angle above 130° or twisting of the double C=N bond and loss of planarity of the quinoid ring. This structural transformation enhances the reactivity of the C=N bond so that 1,2-addition of alcohols becomes possible with formation of sterically unstrained cyclohexadienone structure with sp 3-hybridized C4 carbon atom.

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