Photo-induced Polar Addition of Protic Solvents to Cycloalkenones. Evidence for the Ground-state <I>trans</I> Isomers as Chemically-reactive Intermediates

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概要

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• The photo-induced reaction of cyclic α,β-unsaturated ketones with protic media is described. The irradiation of 2-cycloheptenone or 2-cyclooctenone in various protic solvents (alcohols, acetic acid, water, and diethylamine) results in the formation of Michael-type solvent adducts. The chemically-reactive species have been demonstrated to be the highly strained <I>trans</I> isomers in a ground state. The irradiation of <I>cis</I>-2-cyclononenone affords the stable <I>trans</I> isomer, which reacts in the dark with methyl alcohol at an elevated temperature to give 3-methoxycyclononanone. The irradiation of 2-cyclohexenone in methyl alcohol yields 3-methoxycyclohexanone in a poor yield. The possible existence of <I>trans</I>-2-cyclohexenone is discussed.

• 公益社団法人 日本化学会の論文

著者

• Noyori Ryoji

  Department Of Chemistry And Molecular Chirality Research Unit Nagoya University

• KATO Masao

  Department of Agricultural Chemistry, The University of Tokyo

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