Halogen/metal vs. hydrogen/metal exchange. General or specific site selectivity as exemplified in the camphene series

(Z)-(3,3-dimethylbicyclo[2.2.1]hept-2-ylidene)methyllithium can be readily generated by treatment of (Z)-3-bromomethylene-2,2-dimethylbicyclo[2.2.1]heptane with Me3CLi. At -75 Deg, the organometallic intermediate is configurationally stable and reacts with a variety of electrophiles under stereochem. retention. [on SciFinder (R)]


Published in:
Chemische Berichte, 130, 1, 77-82
Year:
1997
Keywords:
Note:
CAN 126:131647 30-15 Terpenes and Terpenoids Inst. Chimie Organique,Univ. Lausanne,Lausanne,Switz. Journal written in English. 78-83-1 (2-Methyl-1-propanol); 79-92-5 (Camphene); 870-63-3 (3-Methyl-2-butenyl bromide) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselectivity in camphene metalation); 51361-75-2P; 51361-78-5P; 64802-78-4P; 70389-76-3P; 186352-56-7P; 186352-62-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselectivity in camphene metalation); 51361-81-0P; 54382-52-4P; 54382-53-5P; 57566-92-4P; 58437-72-2P; 63028-14-8P; 64802-77-3P; 186352-57-8P; 186352-58-9P; 186352-59-0P; 186352-60-3P; 186352-61-4P; 186352-63-6P; 186352-64-7P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselectivity in camphene metalation)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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