期刊
TETRAHEDRON
卷 61, 期 43, 页码 10262-10276出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.08.035
关键词
sulfoxide-magnesiurn exchange reaction; magnesium alkylidene carbenoid; alkenylation; ortho-alkenylated arylamine; theoretical study
1-Chlorovinyl p-tolyl sulfoxides were synthesized from ketones and chloromethyl p-tolyl sulfoxide in high yields. Treatment of the sulfoxides with isopropylmagnesium chloride at -78 degrees C in toluene gave magnesium alkylidene carbenoids (alpha-chloro alkenylmagnesium chlorides), which were treated with N-lithio arylamines to afford ortho-alkenylated arylamines in moderate yields. The reaction, in some cases, proceeded in a highly stereospecific manner at the carbon bearing the chlorine and the sulfinyl group. The structures of the alpha-chloro alkenylmagnesium chlorides and the reactivity of the N-lithio meta-substituted anilines were studied at the B3LYP and MP2 levels of theory with the 6-31(+)G* basis set. This reaction offers a quite novel and direct alkenylation of arylamines at the ortho-position of the aromatic ring. (c) 2005 Elsevier Ltd. All rights reserved.
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