Structure of (+)-[S-(E)]-N-(alpha-methylbenzylidene)-p-toluenesulfinamide.
Structure of (+)-[S-(E)]-N-(alpha-methylbenzylidene)-p-toluenesulfinamide.
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( )-[S-(E)]-N-(α-甲基亚苄基)-对甲苯亚磺酰胺的结构。
DOI：
10.1107/s0108270190006783
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发表时间：
1991
期刊：
影响因子：
--
通讯作者：
Saha,S
中科院分区：
文献类型：
--
作者：
Robinson,PD;Hua,DH;Chen,JS;Saha,S
C, sH, sNOS, M,= 257.35, monoclinic, P2,, a= 7.710 (2), b= 5.903 (5), c= 14.700 (3) A,/3= 91.48 (2), V= 668-8 (6) A3, Z= 2, Dx= 1.278 gcm-3, A (Mo Kt~)= 0.71069/~,/z= 2.18 cm-1, F (000)= 272, T= 296 K, R= 0-043, 944 unique observed reflections. This is the first structure determination of an N-alkylidenesulfinamide. The~ N bond is distorted and lengthened presumably because of the steric interaction and electron-withdrawing effect of the sulfinyl group. The non-planar conformation is also a result of repulsive steric interaction. The configuration at~ N is trans. The title compound was obtained from the displacement reaction of (-)-l-menthyl (S)-p-toluenesulfinate with methyllithium. Introduction. We have recently studied some asym-metric reactions of chiral N-alkylidenesulfinamides. Their preparation as reported (Cinquini & Cozzi, 1977a) involved the reaction of an alkyl or aryl Grignard reagent with benzonitrile and subsequent reaction with (-)-l-menthyl (S)-p-toluenesulfinate (I). However, the yields-were low and the stereoche-mistry at~ N of the N-alkylidenesulfinamides was not reported. We found that treatment of methyl-magnesium bromide with benzonitrile followed by sulfinate (I) gave only 12% yield of (+)-[S-(E)]-N (a-methylbenzylidene)-p-toluenesulfinamide (II). The use of methyllithium instead of methylmagnesium
