Tetrahedron Letters p. 4347 - 4348 (1993)
Update date:2022-08-04
Topics:
Fong, Mei C.
Schiesser, Carl H.
Thiohydroxamic esters (3) derived from the O-carboxymethyl oxime derivatives (2) of 2-(benzylseleno)-benzaldehyde (1: R = H), 2-(benzylseleno)acetophenone (1: R = Me) and 2-(benzylseleno)propiophenone (1: R = Et) decompose smoothly, upon irradiation, with the loss of carbon dioxide and formaldehyde to give the 1,2-benzoselenazoles (5). The reaction presumably involves the iminyl radical intermediate (4) which undergoes intramolecular free-radical homolytic substitution at selenium to afford the product (5).
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