D. Seyferth, R. Lambert
Apr 15, 1975
Citations
0
Influential Citations
39
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract The reaction of isopropylmagnesium chloride in THF with gem -dibromocyclopropanes gave α-bromocyclopropylmagnesium chloride compounds. When the reaction is carried out at room temperature, these are unstable and carbene-derived products are obtained. At about −70° these reagents are stable and can be used in synthesis. Protolysis gives a mixture of syn and anti isomers when these are possible, but when these Grignard reagents are treated with trimethyltin chloride, only the isomer with the trimethylstannyl substituent in the anti position is obtained. Treatment of syn -7-bromo- anti -7-trimethylstannylnorcarane with n-butyllithium at −95° gave only syn -7-bromo- anti -7-lithionorcarane; stereospecific reactions of this reagent with CO 2 and hexachloroethane are described. In situ Grignard-Wurtz reactions were used to prepare 7,7-bis(trimethylsilyl)- and 7,7-bis(trimethylstannyl)norcarane.