THE REARRANGEMENT OF 4,4-DIPHENYLCYCLOHEXA-2,5-DIENYLIDENE

DOI: 10.1016/0040-4020(82)80085-9

Source and publish data:

Tetrahedron p. 3737 - 3744 (1982)

Update date:2022-09-26

Topics:

Authors:

Freeman, Peter K.

Swenson, Karl E.

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Article abstract of DOI:10.1016/0040-4020(82)80085-9

Pyrolytic decomposition of the Li salt of the tosylhydrazone of 4,4-diphenyl-2,5-cyclohexadienone produces a mixture of biphenyl, o-terphenyl, p-terphenyl, methyl-o-terphenyl and the azine of 4,4-diphenyl-2,5-cyclohexadienone (13).Insight into the reaction pathway was provided by the pyrolytic decomposition of 2-deuterio tosylhydrazone 8a which generates o-terphenyl 10a and 10b in a ratio of 69:31.These results are interpreted in terms of the carbene rearrangements of Schemes 2, 3 and 5.

Full text of DOI:10.1016/0040-4020(82)80085-9

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