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Synthesis 1992; 1992(11): 1073-1075
DOI: 10.1055/s-1992-26304
short paper
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A Facile Synthetic Route to 1,1-Disubstituted 2,3-Dihydro-1H-benz[f]indene-4,9-diones

Sitaram Pal* , Bimal K. Banik, Usha Ranjan Ghatak
  • *Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700 032, India
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Publication Date:
17 September 2002 (online)

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A facile synthetic route is described for 1,1-dimethyl and 1-methoxy-carbonyl-1-methyl substituted 2,3-dihydro-1H-benz[f]indene-4,9-diones 7a, 7c and 7d from the corresponding 1,2,3,4-tetrahydrofluorenes 2a, 2c, and 2d involving ruthenium-catalyzed periodate oxidation of the tetrasubstituted double bond to the respective 6,7,8,9,10,11-hexahydro-5,10-dioxo-5H-benzocyclononenes 3a, 3c and 3d, cyclization-dehydration (aromatization) and methylation to 2,3-dihydro-4-methoxy-1H-benz[f]indenes 6a, 6c and 6d, followed by oxidation with pyridinium chlorochromate/Celite. The only exception to this trend is 2b, which on ruthenium-catalyzed Periodate oxidation directly affords 7b