Oxidation of organic compounds with cerium (IV). VIII. Oxidation of bicyclo [2.2. 1]-2-heptanols and bicyclo [2.2. 2]-2-octanol

WS Trahanovsky, PJ Flash…

Index: Trahanovsky,W.S. et al. Journal of the American Chemical Society, 1969 , vol. 91, # 18 p. 5068 - 5072

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Citation Number: 34

Abstract

Abstract: It is reported that oxidation of either em-or endo-2-norbornanol with 2 equiv of ceric ammonium nitrate in 50% aqueous acetonitrile at 50'gave three major products, 3-and 4- cyclopenteneacetaldehydes and 3-ni-tratocyclopentaneacetaldehyde. Oxidation of bicyclo [2.2. 21-2-octanol under these conditions was found to give 4-~ yclohexeneacetaldehyde, and cis-and trans-4-nitratocyclohexaneacetaldehydes. Structure proofs for these products ...