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Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIII. Reactions of N-alkyl(aryl, trifluoromethyl)sulfonyl-, N-arylsulfinyl- and N-arylsulfanyl-1,4-benzoquinone monoimines with alcohols |
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| Authors: | A. P. Avdeenko S. A. Konovalova O. N. Mikhailichenko A. A. Santalova G. V. Palamarchuk O. V. Shishkin |
| Affiliation: | 1. Donbass State Engineering Academy, Kramatorsk, 84313, Ukraine 2. Institute of single crystals, National Academy of Sciences of Ukraine, Kharkov, Ukraine 3. Karazin Kharkov National University, Kharkov, Ukraine |
| Abstract: | Steric strains arising between the substituent atoms at nitrogen (S, SO, or SO2) and the methyl group located in positions 3 or 5 of the quinoid ring of 3,5-dimethyl-substituted quinone monoimines lead to the increased angle C=N-S. As a result in these quinone monoimines the reactions of 1,2-addition become thermodynamically possible since the formation of quinolide structures with the sp3-hybridized carbon atom removes the steric strain. |
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