ORGANIC-CHEMISTRY OF DICHLOROSILANE - ADDITIONS TO CONJUGATED AND UNCONJUGATED DIENE SYSTEMS FOLLOWED BY INTRA-MOLECULAR CYCLIZATIONS

The addition of dichlorosilane to both conjugated and unconjugated dienes was studied in the presence of chloroplatinic acid as a catalyst. The mode of addition to conjugated dienes was predominantly by a 1, 4 pathway. With unconjugated dienes, addition to a terminal double bond was much faster than to internal double bonds and hence provided a convenient method for the synthesis of alkenyldichlorosilanes. The latter were cyclized in an intramolecular fashion with catalytic amounts of chloroplatinic acid to form novel cyclic and bicyclic silicon-containing heterocycles. In this fashion the very novel 7, 7-dichloro-7-silanorbornane was prepared. Nucleophilic displacement reactions on the silicon atom in this novel compound were also studied. © 1979, American Chemical Society. All rights reserved.