345927-80-2Relevant academic research and scientific papers
Acid-Catalyzed Intramolecular C-Alkylation in β,γ-Unsaturated Diazomethyl Ketones. 3. A Simple Synthetic Route to Hexahydro-4,9a-ethano-1H-fluoren-11-ones, Hexahydro-6H-pentalenoindan-4-ones, and Hexahydrocyclobutafluoren-2(1H)-ones
Roy, Subhas C.,Satyanarayana, Gutta O. S. V.,Ghatak, Usha Ranjan
, p. 5361 - 5368 (2007/10/02)
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-pentalenoindan-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.
