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Note | Regular issue | Vol 51, No. 5, 1999, pp.1073-1078
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8317
Preparation of 1,4-Dioxenes from α-Diazo-β-ketoesters

Ramona Hilgenkamp, John B. Brogan, and Charles K. Zercher*

*Department of Chemistry, College of Engineering and Physical Sciences, Parsons Hall, University of New Hampshire, Durham, NH 03824, U.S.A.

Abstract

A novel preparation of 1,4-dioxenes is reported in which a rhodium carbenoid generated from an α-diazo-β-ketoester reacts with a 1,2-diol. Insertion of the carbenoid into the O-H bond followed by hemiacetal formation and acid-catalyzed dehydration generates the targeted 1,4-dioxene.