Cyclopropanes. XXV. Cyclopropyl anion
Cyclopropanes. XXV. Cyclopropyl anion
复制标题
环丙烷。
DOI：
10.1021/ja00711a040
复制
发表时间：
1970
影响因子：
15
通讯作者：
J. M. Motes
中科院分区：
文献类型：
--
作者：
H. Walborsky;J. M. Motes
Therate of hydrogen-deuterium exchange and rate of racemization of 2, 2-diphenylcyclopropylnitrile (1) and its acyclic analog 2-methyl-3, 3-diphenylpropionitrile (2) have been investigated. The cyclic nitrile ex-hibits a very high degree of retention of configuration in methanol,/-butyl alcohol, and methanol-dimethyl sulfoxide (10: 90) using sodium alkoxide as the base. In contrast, extensive racemization was observed for the acyclic nitrile. Small kinetic isotope effects (Ah/Kd~ 2) were observed with both nitriles. These observations in con-junction with results of ancillary studies are interpreted by us to show that proton abstraction by base is not rate determining in both theexchange and racemizationreaction of 2, 2-diphenylcyclopropylnitrile (1).
