A mechanistic study of the rhodium-catalyzed cyclization of 4-hexenals. Reactions of deuterio-4-hexenals

RE Campbell Jr, CF Lochow, KP Vora…

Index: Campbell, Richard E.; Lochow, Charles F.; Vora, Krishnakant P.; Miller, Roy G. Journal of the American Chemical Society, 1980 , vol. 102, # 18 p. 5824 - 5830

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Citation Number: 76

Abstract

Abstract: In independent experiments, four carbons in the 4-pentenal skeleton have been labeled with deuterium or methyl and the fate of each label has been determined as the pentenal was transformed into a cyclopentanone derivative by RhCI (PPh3) 3 (1) at 24-26" c. The catalyst converted 4-hexenal to 2-methylcyclopentanone (2) in CHCI3 and C6H6. Approximately equivalent amounts of hydrocarbon decarbonylation products and RhCI ( ...