Chemistry of 2-Carbenabicyclonona-3,6,8-triene

Article abstract of DOI:10.1021/jo00132a012

Pyrolysis of the lithium salt of the tosylhydrazone of bicyclo<3.2.2>nona-3,6,9-trien-2-one (10) produces indene and 7-ethynyl-1,3,5-cycloheptatriene.As an aid in analyzing likely carbene to carbene rearrangements, the pyrolytic decomposition of the lithium salt of tricyclo<6.1.0.0^4,9>nona-2,6-dien-5-one tosylhydrazone was studied and found to result in the formation of indene as the sole volatile product.The decomposition of the lithium salt of tosylhydrazone 10 is discussed in terms of carbenes 13, 15, 16, and 6a and allene 14.