Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen??Displacement Reactions

K Mlinarić??Majerski, J Veljković…

Index: Mlinaric-Majerski, Kata; Veljkovic, Jelena; Kaselj, Mira; Marchand, Alan P. European Journal of Organic Chemistry, 2004 , # 13 p. 2923 - 2927

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Abstract

Abstract Three dihaloadamantanes [ie, 2-bromo-1-(chloromethyl) adamantane (1), 1- (bromomethyl)-2-chloroadamantane (2) and 2-bromo-1-(bromomethyl) adamantane (3)] were synthesized, and their corresponding ring-closing reactions, performed by using Na metal or alkyllithium reagents, were studied. Compound 1 reacted with Na in toluene or in tetraglyme to afford 1, 2-methanoadamantane (4) as the major product. However, the ...