Preparation Of α-sulfon Yl Vinyl Magnesium Reagents And Their Application In Organic Sythesis

In this thesis, the carbomagnesiation of acetylenic sulfone and its further reaction with p-tolylsulfonyl imines orα,β-unsaturated ketones were investigated. Various polysubstituted alkenes were synthesized regio- and stereoselectivitily. The thesis consists of the following two parts.1. The carbomagnesiation of acetylenic sulfones and its further reaction with p-tosylsulfonyl imines in the presence of catalytic CuCN was investigated.α-Sulfonyl vinyl magnesium bromide was obtained by carbomagnesiation of acetylenic. Polysubstituted substituted vinyl sulfones were synthesized by the reaction of the obtained vinyl magnesium bromide with p-tosylsulfonyl imines. Polysubstituted vinyl sulfones containing allyl amine and 1, 4-diene structural unit were obtained regio- and stereo selectively when the allyl magnesium bromide was used. The molecular structure of 1, 3-diphenyl-N, 2-di(p-tolylsulfonyl)-2, 5-hexdiene-1-amine was determined by X-ray diffraction analysis. All the products were characterized by ¹H NMR,¹³C NMR,IR and MS.2. The three-component tandem reactions of Grignard reagents, acetylenic sulfone and a,β-unsaturated ketones in the presence of catalytic CuCN were investigated,γ,δ- Unsaturated ketones were obtained when benyl magnesium bromine was used and polysubstituted pyran derivations were obtained when allyl magnesium bromine was used. The products were characterized by ¹HNMR,¹³C NMR,IR and MS.