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Communication | Regular issue | Vol 63, No. 1, 2004, pp.1-4
Published online, 14th November, 2003
DOI: 10.3987/COM-03-9911
Benzodioxole Chemistry. 5. Dramatic Substituent Effect in the Reaction of Carbonyl-bridged Cyclic Carbonates with Methoxide Ion

William S. Grove and Ernest A. Harrison Jr.*

*Department of Chemistry, The Pennsylvania State University, York Campus, 1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.

Abstract

Benzodioxolediones (2c-e) undergo high-yield conversion to cyclopentenones (3c-e) in K2CO3/MeOH at room temperature, while analogs (2a) and (2b) yield exclusively cyclohexadiene carboxylates (1a and 1b) under these conditions. Isolation of intermediate 6(R,R’=Me R”=Ph) from the reaction of 2c with K2CO3/MeOH at 5-10 °C suggests that 3 is formed in a process triggered by attack of OMe(-) at the ester carbonyl of 2.