Issue 7, 1991

Photoreaction of a stable thioaldehyde 2,4,6-tri-tert-butylthiobenzaldehyde

Abstract

The photochemical reaction of the only isolable aromatic thioaldehyde ArCHS (1; Ar = 2,4,6-tri-tert-butylphenyl) in alkaline medium yields ArCH2CH2Ar (2), ArCH2SCH2Ar (3), 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1H-2-benzothiine (4) and ArMe (5). A radical mechanism which accounts for the formation of these compounds is proposed, mainly on the basis of the direct observation (EPR spectroscopy) of a number of radicals such as ArCHS˙(A), ArCHCH2Ar (B), and ArCH2˙(D). Results of scrambling of deuterium atoms confirmed the structure of these radicals through interpretation of the corresponding EPR spectra.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1991, 1045-1049

Photoreaction of a stable thioaldehyde 2,4,6-tri-tert-butylthiobenzaldehyde

M. A. Cremonini, L. Lunazzi, G. Placucci, N. Kumon, A. Ishii, T. Kawashima and R. Okazaki, J. Chem. Soc., Perkin Trans. 2, 1991, 1045 DOI: 10.1039/P29910001045

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