Tetrahedron

Aspects of the 2, 3-trimethylenenorbornane-adamantane rearrangement: Selective halogenation of adamantane and 1-methyladamantane

H Hamill, A Karim, MA McKervey

Index: Hamill,H. et al. Tetrahedron, 1971 , vol. 27, p. 4317 - 4322

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Citation Number: 11

Abstract

Aluminium bromide-catalyzed bromination of either exo-or endo-2, 3- trimethylenenorbornane gives 1, 3, 6-tribromoadamantane, 1, 3, 5-tribromoadamantane and 1, 2, 3, 5, 6, 7-hexabromonaphthalene; intermediate products of the reaction could not be detected. Methods for the selective bridgehead mono-and dichlorination of adamantane and 1-methyladamantane are described. Hydrolysis of 1, 3-dichloroadamantane and 5-methyl- ...