Photochemical Deuteration of <I>ortho</I>-Substituted <I>N</I>-(Diphenylmethylene)acetamides

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概要

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• The alkyl hydrogens of <I>N</I>-(2-alkyldiphenylmethylene)acetamides were found to be readily replaced with deuterium on irradiation in deuteriomethanol (CH<SUB>3</SUB>OD). It is proposed that the deuteration proceeds <I>via</I> an enamide isomer produced by intramolecular hydrogen transfer from the <I>o</I>-alkyl group to the excited C=N double bond. An intermolecular hydrogen atom abstraction pathway was excluded because neither <I>N</I>-(4-methyldiphenylmethylene)acetamide in deuteriomethanol(CH<SUB>3</SUB>OD) nor diphenylmethane in deuteriomethanol(CH<SUB>3</SUB>OD) in the presence of <I>N</I>-(diphenylmethylene)acetamide was deuterated. Intramolecular hydrogen abstraction is essential for the deuteration, because no deuteration occurs on irradiation of 2-methylbenzophenone semicarbazone which undergoes no photoreduction. The difference in reactivities of the <I>ortho</I>-substituted imines between in solution and in a rigid matrix is discussed from the viewpoint of <I>syn-anti</I> isomerization.

• 公益社団法人 日本化学会の論文

著者

• Toshima Naoki

  Department Of Applied Chemistry

• Hirai Hidefumi

  Department Of Industrial Chemistry Faculty Of Engineering Science University Of Tokyo

• Saeki Masaru

  Department of Industrial Chemistry, Faculty of Engineering The University of Tokyo

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