Carbenoid reactions by means of diethylcadmium and gem-diiodoalkane
作者:J. Furukawa、N. Kawabata、T. Fujita
DOI:10.1016/0040-4020(70)85024-4
日期:——
corresponding reaction with diethylzinc. Phenylsubstituted cyclopropane was obtained from the reaction of olefin with diethylcadmium and benzal iodide. The reaction was found to favour the syn isomer but less than the corresponding reaction with diethylzinc. Phenylpropadienes were obtained from phenylacetylenes, diethylcadmium and gem-diiodoalkane. On the other hand, in the corresponding reaction with diethylzinc
chlorine tocis-cyclooctene yields thetrans-dichloride, which has a dipole moment of 3·1D, that is slightly solvent dependent. The correspondingcis-dichloride was not obtained by the chlorination of thetrans-olefin, but was synthesized indirectly, and found to have a dipole moment of 2·3D, which is also solvent dependent. The addition of halogen totrans-cyclooctene was shown to yield a complex mixture of products
prepared in 32–96% yield by the reaction of olefins with ethylidene iodide and diethylzinc. The reaction is electrophilic, and proceeds stereospecifically. In the case of the reaction with 1,2-disubstituted olefins, cis and transolefins affords cyclopropane derivatives whose configurations with respect to the substituents from original olefins are cis and trans, respectively.