Kinetic deuterium isotope effects as evidence for a common ion-pair intermediate in solvolytic elimination and substitution reactions of 1,1-diphenylethyl chloride
作者:Alf Thibblin、Harvinder Sidhu
DOI:10.1021/ja00045a010
日期:1992.9
Solvolysis of 1,1-diphenyl-1-chloroethane (1-Cl) in acetonitrile at 25 o C provides the elimination product 1,1-diphenylethene (3). Addition of water or methanol to the acetonitrile increases the rate of elimination and gives rise to a second product, 1,1-diphenyl-1-hydroxyethane (1-OH) or 1,1-diphenyl-1-methoxyethane (1-OMe). The deuteriated analogue, 1,1-diphenyl-1-chloro[2,2,2- 2 H3]ethane (d-1-Cl)
1,1-二苯基-1-氯乙烷 (1-Cl) 在 25 o C 下在乙腈中的溶剂分解提供消除产物 1,1-二苯基乙烯 (3)。向乙腈中加入水或甲醇可提高消除速率并产生第二个产物 1,1-二苯基-1-羟基乙烷 (1-OH) 或 1,1-二苯基-1-甲氧基乙烷 (1-OMe) . 氘代类似物 1,1-二苯基-1-氯[2,2,2-2 H3]乙烷 (d-1-Cl) 反应较慢