Experimental Probe for Hyperconjugative Resonance Contribution in Stabilizing the Singlet State of 2,2-Dialkoxy-1,3-diyls:  Regioselective 1,2-Oxygen Migration

Experimental Probe for Hyperconjugative Resonance Contribution in Stabilizing the Singlet State of 2,2-Dialkoxy-1,3-diyls:  Regioselective 1,2-Oxygen Migration

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 migratio...

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Veröffentlicht in:Journal of the American Chemical Society 2006-06, Vol.128 (24), p.8008-8014
Hauptverfasser: Abe, Manabu, Hattori, Masanori, Takegami, Akinobu, Masuyama, Araki, Hayashi, Takashi, Seki, Shu, Tagawa, Seiichi
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Chemistry
Exact sciences and technology
Free radicals chemistry
Organic chemistry
Reactivity and mechanisms
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container_end_page 8014
container_issue 24
container_start_page 8008
container_title Journal of the American Chemical Society
container_volume 128
creator Abe, Manabu
Hattori, Masanori
Takegami, Akinobu
Masuyama, Araki
Hayashi, Takashi
Seki, Shu
Tagawa, Seiichi
description 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.
doi_str_mv 10.1021/ja0617688
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subjects Chemistry
Exact sciences and technology
Free radicals chemistry
Organic chemistry
Reactivity and mechanisms
title 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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