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Synthesis and reactivity of 3-(trichlorogermyl)propanoic acid and 3-(triphenylgermyl) propanoic acid
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 27 AUG 2010 , DOI: 10.1002/cjoc.19980160212 Zeng Qiang , Zeng Xian-Shun , Wang Qing-Min , Cui Tao , Zhang Zhong-Biao
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 27 AUG 2010 , DOI: 10.1002/cjoc.19980160212 Zeng Qiang , Zeng Xian-Shun , Wang Qing-Min , Cui Tao , Zhang Zhong-Biao
3-(Trichlorogermyl)propanoic acid (1a) reacts with phenylmagnesium bromide in molar ratio 1:4 to give 3-(triphenylgermyl)propanoic acid (2a). In the compounds 1a and 2a the β-carboxylic functional group shows some unusual properties when they react with excess of phenylmagnesium bromide. The compound 1a reacts with phenylmagnesium bromide in molar ratio 1:5 to give phenyl 2-(triphenylgermyl)ethylketone (3a) and in molar ratio 1:6 to give 1,1-diphenyl-3–(triphenylgermyl)propanol (4a). The compound 2a reacts with phenylmagnesium bromide in molar ratio 1:2 to give 3a and in molar ratio 1:3 to give 4a also. Dehydration of the compound 4a with dilute hydrochloric acid seems especially easy. Moreover, the compound la reacted with phenylmagnesium bromide in molar ratio 1:6, then the mixture was treated with dilute hydrochloric acid to give 1,1-diphenyl-3 (triphenylgermyl)-1-propene (5a) in one pot reaction. Alkyl Ge–C bond in the compound 5a can be cleaved selectively by lithium aluminium hydride (LiAlH4) in good yield.
中文翻译:
3-(三氯锗烷基)丙酸和3-(三苯基锗烷基)丙酸的合成与反应性
3-(三氯锗烷基)丙酸(1a)与苯基溴化镁以1∶4的摩尔比反应,得到3-(三苯基锗烷基)丙酸(2a)。在化合物1a和2a中,β当羧基羧酸官能团与过量的苯基溴化镁反应时,它们显示出一些不同寻常的性质。化合物1a与苯基溴化镁以1:5的摩尔比反应,生成苯基2-(三苯基锗基)乙基酮(3a),以1:6的摩尔比生成1,1-二苯基-3–(三苯基锗基)丙醇(4a)。化合物2a与苯基溴化镁以摩尔比1∶2反应得到3a,并且以摩尔比1∶3反应也得到4a。用稀盐酸使化合物4a脱水似乎特别容易。此外,化合物1a与苯基溴化镁以1∶6的摩尔比反应,然后将混合物用稀盐酸处理,在一次反应中得到1,1-二苯基-3(三苯基锗烷基)-1-丙烯(5a)。化合物5a中的烷基Ge–C键可以被氢化铝锂(LiAlH4)收率好。
更新日期:2017-01-31
中文翻译:
3-(三氯锗烷基)丙酸和3-(三苯基锗烷基)丙酸的合成与反应性
3-(三氯锗烷基)丙酸(1a)与苯基溴化镁以1∶4的摩尔比反应,得到3-(三苯基锗烷基)丙酸(2a)。在化合物1a和2a中,β当羧基羧酸官能团与过量的苯基溴化镁反应时,它们显示出一些不同寻常的性质。化合物1a与苯基溴化镁以1:5的摩尔比反应,生成苯基2-(三苯基锗基)乙基酮(3a),以1:6的摩尔比生成1,1-二苯基-3–(三苯基锗基)丙醇(4a)。化合物2a与苯基溴化镁以摩尔比1∶2反应得到3a,并且以摩尔比1∶3反应也得到4a。用稀盐酸使化合物4a脱水似乎特别容易。此外,化合物1a与苯基溴化镁以1∶6的摩尔比反应,然后将混合物用稀盐酸处理,在一次反应中得到1,1-二苯基-3(三苯基锗烷基)-1-丙烯(5a)。化合物5a中的烷基Ge–C键可以被氢化铝锂(LiAlH4)收率好。