Acid-Catalyzed Hydrolysis of Some <i>N</i>,<i>N</i>-Dibenzylalkanesulfinamides in 50% Acetonitrile–Water
作者:Mrityunjoy Datta、Alan J. Buglass
DOI:10.1080/10426507.2012.704105
日期:2013.6.1
bimolecular neutral, acid-catalyzed, and acid-dependent nucleophilic (halide ion) catalysis pathways. The last-named is predominant in reactions in HBr solutions, but in HCl solutions, the acid-catalyzed pathway is predominant. The results indicate that both steric and electronic effects are important in these reactions. There appears to be no mechanistic switchover in the series 1→4. GRAPHICAL ABSTRACT
摘要 研究了一些 N,N-二苄基链烷亚磺酰胺 (RSONH(CH2Ph)2; 1, R = Me; 2, R = iPr; 3, R = tBu; 4, R = 1-金刚烷基) 50% ( v:v) 氢溴酸和盐酸的乙腈-水溶液,主要在 44.8 °C,使用紫外 (UV) 分光光度法确定伪一级速率常数。发现这些化合物通过同时发生的双分子中性、酸催化和酸依赖性亲核(卤离子)催化途径水解。后一种反应在 HBr 溶液中占主导地位,但在 HCl 溶液中,酸催化途径占主导地位。结果表明空间和电子效应在这些反应中都很重要。在系列 1→4 中似乎没有机械转换。图形概要