engleski

Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions

Three dihaloadamantanes [i.e., 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 corresponding reactions, when performed by using 2 and 3 as substrates, produced methyladamantane (5) or 4-methyl-eneprotoadamantane (6) as the major reaction products. The corresponding reactions of 1 and 2 with tBuLi or nBuLi afforded small quantities of 4, 5 and 6 along with the corresponding monohalides, that is, 1-(chloromethyl)adamantane (7) and 2-chloro-1-methyladamantane (8), which constituted the major products of these reactions.

Dihaloadamantanes; Ring closure; Rearrangement; Halogen displacement; Cyclization

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