Mechanistic investigation of an anomalous anchimeric assistance in the acid hydrolysis of the ether linkage. Part 4

被引:7
作者
Arcelli, A [1 ]
Cecchi, R [1 ]
Porzi, G [1 ]
Rinaldi, S [1 ]
Sandri, S [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, Bologna, Italy
关键词
neighbouring group effect; amides; ethers; cleavage reactions; kinetics;
D O I
10.1016/S0040-4020(01)00285-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Kinetic investigation of the acid hydrolysis of N-(methoxyprop-2-yl)benzanilide (1) was performed in 8.84 M HCl and/or DCl at 75.1 degreesC. The formation of 2-(N-phenylamino)propanol (4) was explained and the mechanism, involving an initial ether cleavage anchimerically assisted by the amide group, was clarified. The overall process evolves through three steps involving two intermediates. The rate constants of the individual processes have been determined by UV and H NMR spectroscopic techniques. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4039 / 4043
页数:5
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