80530-76-3Relevant articles and documents
REACTIONS OF CARBENES WITH BICYCLOBUTANES AND QUADRICYCLANE CYCLOADDITIONS WITH TWO ? BONDS
Jackson, James E.,Mock, George B.,Tetef, Merry L.,Zheng, Guo-Xiu,Jones, Maitland Jr.
, p. 1453 - 1464 (1985)
Dicarcomethoxycarbene and dichlorocarbene add to 1,2,2-trimethylbicyclobutane in such a fashion as to suggest a concerted addition in which the central and side bonds are cleaved simultaneously.MNDO calculations support such a pathway and suggest that endo attack on the bicyclobutane is preferred to exo.Reaction of the same two carbenes with quadricyclane gives substituted derivatives of the exo-tricyclo2,4>oct-6-ene system.Although these products rearrange further under the conditions of reaction and/or analysis, they can be shown to be primary products.It is suggested that quadricyclane reacts with carbenes in a concerted fashion.