Ring-Opening Reactions of Anionic Cyclopropyl Compounds. 3

Article abstract of DOI:10.1021/jo01292a016

The reaction of KO-t-Bu in Me₂SO with the tricyclocyclopropyl carbonyl compounds 3a,b was shown to result in the formation of cyclopentadienes and cinnamic acid derivatives 4a,b and 5a,b which were shown to be preceded by intermediates 6a,b.It is suggested that 6a,b rearrange to 4a,b and 5a,b via an unusual electrocyclization followed by a fragmentation.An example of an apparent conrotatory ring opening of a cyclopropyl carbanion or anion radical is presented in the conversion of 8 to 9.