Synthetic communications

A new entry to alkylidenecyclopropanes through a Ramberg-Backlund rearrangement of cyclopropylsulfones

AM Bernard, A Frongia, PP Piras

Index: Bernard, Angela M.; Frongia, Angelo; Piras, Pier P. Synthetic Communications, 2003 , vol. 33, # 5 p. 801 - 817

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Citation Number: 6

Abstract

View all references has been published using the well known Ramberg-Backlund reaction for the synthesis of the bicyclopropylidene. The failure of this attempt was attributed by the authors to the established unreactivity of cyclopropyl halides and sulfonate esters toward displacement reactions due to the adverse hybridization characteristic of external bonds attached to three-membered rings (I strain). They pointed out that α-haloalkyl cyclopropylsulfones might be expected to ...