Organoelement Compounds
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ChemInform Abstract: Mechanistic Definition of Trimethylstannylation of 1,4-Dihalobicyclo-(2.2.1)heptanes: Bridgehead Nucleophilic Substitution Mediated by the Intermediacy of Radicals, Radical Anions, Carbanions, and (2.2.1)Propellane.
First published: May 22, 1990
Abstract
Six dihalobicycloheptanes such as (IV) and (V) are prepared starting with the acid (II) by the methods outlined in the reaction scheme.
ChemInform Abstract
Six dihalobicycloheptanes such as (IV) and (V) are prepared starting with the acid (II) by the methods outlined in the reaction scheme. Their reaction with trimethylstannyllithium (VI) produces bridgehead-stannylated norbornanes such as (VII) - (X). For mechanistic studies, the reactions are also performed in the presence of tert-butylamine as carbanion scavenger or tetraglyme as viscosity increasing agent.
