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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 |
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| Authors: | A. P. Avdeenko S. A. Konovalova V. M. Vasil’eva G. V. Palamarchuk V. N. Baumer O. V. Shishkin |
| Affiliation: | 1. Donbass State Engineering Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine 2. Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkiv, Ukraine 3. Karazin Kharkiv National University, Kharkiv, Ukraine |
| 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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