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EFFECT OF MERCAPTAN ON PHOTOREDUCTION OF ACETONE. NON‐REPAIR HYDROGEN TRANSFER REACTIONS †
Author(s) -
COHEN SAUL G.,
AKTIPIS STELIOS,
RUBINSTEIN HARRY
Publication year - 1969
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1969.tb07219.x
Subject(s) - benzophenone , chemistry , acetone , photochemistry , radical , hydrogen atom , irradiation , organic chemistry , alkyl , physics , nuclear physics
— Ultraviolet (u.v.) irradiation of solutions of benzhydrol in acetone leads to formation of ‐2‐propanol, benzpinacol and some benzophenone, apparently from the free radicals (CH 3 ) 2 COH, II, and (C 6 H 5 ) 2 COH, I. 2‐Propanol is formed more rapidly and benzophenone is formed to a much larger extent and persists longer when the solution contains mesityl mercap‐tan, as radical II is reduced by mercaptan and radical I is oxidized by thiyl radical. The same hydrogen atom transfer reactions, which retard by a repair mechanism the photoreduction of benzophenone by 2‐propanol, accelerate and alter the course of photoreduction of acetone by benzhydrol. Irradiation of acetone leads to 2‐propanol, and this is formed more rapidly in the presence of mercaptan. Irradiation of benzophenone in acetone leads to no apparent reaction. The courses of reaction of the several systems are discussed.