Bulletin of the Chemical Society of Japan p. 2032 - 2039 (1989)
Update date:2022-08-24
Topics:
Shimizu, Nobujiro
Miyahara, Toru
Mishima, Masaaki
Tsuno, Yuho
Transient enols including those of acetaldehyde, acetone, cyclopentanone, 3-pentanone, 2,4-dimethyl-3-pentanone, 2-butanone, and 2-methyl-3-pentanone were trapped photochemically with acetone via a <2+2>cycloaddition and isolated as corresponding 3-oxetanols in reasonable yields in the photolysis of six different secondary alcohols and two alkanones, 3-octanone and hexanal, in acetone solutions.The trapping experiments indicated the photodehydrogenation of unsymmetrical alcohols, 2-butanol and 2-methyl-3-pentanol, in acetone to be highly regioselective in preference for the formation of the less alkylated enol.
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