Journal of Organic Chemistry p. 5361 - 5368 (1982)
Update date:2022-08-03
Topics:
Roy, Subhas C.
Satyanarayana, Gutta O. S. V.
Ghatak, Usha Ranjan
C-Alkylation rearrangements of the tetrahydrofluorene diazoacetyl derivatives 1a-e with tetrahydrofluoboric acid in nitromethane and toluene-p-sulfonic acid in boiling benzene are shown to give, in good to excellent yields, the hydroxycyclopentanones 3a-e and the tetrahydro-6H-pentaleno<6a,1-a>indan-4-ones 4a-e, respectively.These undergo stereospecific catalytic hydrogenation to the respective bridged cyclopentanones 14a-e and the hexahydroindan-4-ones 15a-e.The cyclization of the diazo ketones 1c-e with trifluoroacetic acid in chloroform gives the respective angularly fused unsaturated cyclobutanones 2c-e, which undergo highly stereoselective catalytic hydrogenation to the corresponding trans angularly substituted hexahydrofluorene-cyclobutanone compounds 16c-e.
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