Synthesis and chemistry of 9-homonoradamantane (tricyclo [3.3. 2.03, 7] decane)

Z Majerski, S Djigas, V Vinkovic

Index: Majerski,Z. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 23 p. 4064 - 4069

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Citation Number: 9

Abstract

9-Homonoradamantane (tricycl0 [3.3. 2.0~~~] decane) is one of the few unknown adamantane isomers. Two independent synthetic routes to this system were developed: the benzilic acid ring contraction of 10-homo-protoadamantane-4, 5-dione leading to 2- substituted 9-homonoradamantanes and the diazomethane homologation of 9- noradamantanone to 9-homonoradamantan-9-one (10). The parent hydrocarbon, 9- ...