Journal
ORGANIC LETTERS
Volume 5, Issue 19, Pages 3407-3409Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol034997x
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A barrelene derivative fragments to afford benzene and trappable 1,2,3-tricyanocyclopropene. The barrelene anion fragments more easily to liberate benzene and the 1,2,3-tricyanocyclopropenyl anion, which is not trappable or stable in solution. However, the major thermal product from the barrelene anion is a rearranged allyl anion that is formed by disrotatory cleavage of the cyclopropyl ring, a formally Woodward-Hoffmann-forbidden process. Several proposals are offered to rationalize this forbidden rearrangement.
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