Journal of the Chemical Society. Perkin transactions I p. 263 - 267 (1991)
Update date:2022-08-02
Topics:
Jones, David W.
Pomfret, Alan
The relatively stable o-quinodimethane 7 has been prepared by photodecarbonylation of the 1,3-diphenylinden-2-one-norbornene adduct 5.Reactions of 7 with phenyltriazolinedione, sulphur dioxide and triplet oxygen all occur to the less hindered face of the diene system terminating at the α,α'-positions of the o-quinodimethane.The same face of the same diene system is involved in forming the major carbonyl iron complex, 12, of 7.Both thermolysis and acid-catalysed rearrangement of 7 give the dihydronaphthalene 10.The 1,5-sigmatropic hydrogen shift of 7 that would give 10 is slow at 140 deg C.
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