7-Halo-7-methylnorcaranes (I) and 7,7-dimethylnorcarane (II) are formed via replacement of halogen by Me during the reaction of cyclohexene (III) with carbenes (carbenoids) and MeLi. Thus, III is treated with CHClF2 or CCl2F2 and MeLi to give a mixt. of 7-chloro-7-fluoronorcarane (IV), I, and II. 1,1-Difluoro-2,2-dimethylcyclopropanes (V) are obtained from Me2C:CHMe and Me2C:CH(CH2)2CH(OEt)2. [on SciFinder (R)]
Title
Alkyl/halogen substitution in carbenes (carbenoids): a route to new cyclopropane derivatives
Published in
Angewandte Chemie, International Edition
Volume
10
Issue
2
Pages
138-9
Date
1971
Note
CAN 74:141049 24 Alicyclic Compounds Org.-Chem. Inst.,Univ. Heidelberg,Heidelberg,Fed. Rep. Ger. Journal 0570-0833 written in English. 1460-19-1P; 26650-62-4P; 31707-69-4P; 31754-77-5P; 31754-78-6P; 31754-79-7P; 31754-80-0P; 31772-74-4P; 31772-75-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 917-54-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with methane halo derivs. and olefins); 75-45-6; 75-71-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with methyllithium and olefins)
Record creation date
2006-03-03