Experimental probe for hyperconjugative resonance contribution in stabilizing the singlet state of 2,2-dialkoxy-1,3-diyls: Regioselective 1,2-oxygen migration |
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| Authors: | Abe Manabu Hattori Masanori Takegami Akinobu Masuyama Araki Hayashi Takashi Seki Shu Tagawa Seiichi |
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| Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan. abe@chem.eng.osaka-u.ac.jp |
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| Abstract: | A detailed study of the regioselectivity of 1,2-oxygen migration was conducted using the unsymmetrically substituted singlet 2,2-dialkoxy-1,3-diarylcyclopentane-1,3-diyls 5. The alkoxy group selectively migrates to the electron-donating p-methoxyphenyl-substituted carbon. The regioselective migration of oxygen clearly indicates a hyperconjugative resonance structure, that is, zwitterionic characteristics, in singlet 2,2-dialkoxy-1,3-diyls. This represents the first attempt to experimentally probe the contribution of hyperconjugation to stabilizing the singlet state. |
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