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Synthesis 1985; 1985(12): 1142-1144
DOI: 10.1055/s-1985-31454
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Catalytic cis to trans Conversions; Dihydroxybicyclo[2.2.1]heptane and 1,2-Dihydroxyindane

Jay E. Taylor*
  • *Department of Chemistry, Kent State University, Kent, Ohio 44242, U. S. A.
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Publication Date:
27 September 2002 (online)

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cis-2-exo, 3-exo-Dihydroxybicylo[2.2.1]heptane (2) was isomerized in aqueous solution by an improved procedure to the corresponding trans-glycol 3 in 71% yield, using Raney nickel at 80°C for 56 hours. Similarly, cis-1,2-dihydroxyindane (5) was isomerized by Raney nickel at 60°C m 42 hours giving 31% trans-1,2-dihydroxyindane (7).