82507-52-6Relevant academic research and scientific papers
STUDIES ON THE TRICYANOCYCLOPROPENYL SYSTEM
Breslow, Ronald,Cortes, David A.,Jaun, Bernhart,Mitchell, R. David
, p. 795 - 798 (1982)
Chlorination of tricyanocyclopropane is observed to lead directly to trichlorotricyanocyclopropane which undergoes a remarkable reductive conversion to hexacyanobenzene.The synthesis of mono- and dichlorotricyanocyclopropane (4 and 5) and their use as potential precursors for tricyanocyclopropenyl anion is described.
A Forbidden Rearrangement
Leivers, Martin,Tam, Iris,Groves, Kevin,Leung, David,Xie, Yuli,Breslow, Ronald
, p. 3407 - 3409 (2007/10/03)
(Equation presented) 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.
