73733-09-2Relevant articles and documents
EFFECT OF THE STRUCTURE OF BICYCLIC CARBENES ON THE DIRECTION OF THEIR STABILIZATION
Levashova, T. V.,Semeikin, O. V.,Balenkova, E. S.
, p. 53 - 56 (2007/10/02)
By pyrolysis of the sodium salts of bicyclooctan-2-one and bicyclononan-2-one tosylhydrazones the corresponding carbenes were generated.The first of them undergoes fragmentation with the formation of 1-octen-7-yne and rearrangement to bicyclooct-6-ene, and the second rearranges to bicyclodec-8-ene and forms the products from transannular insertion, i.e., tricyclo2,4>decane and tricyclo2,4>decane.The difference in the direction of stabilization in these carbenes is due to the geometry of the arrangement of the three-membered ring in relation to the vacant p orbital.