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

Authors
Arcelli, A Cecchi, R Porzi, G Rinaldi, S Sandri, S
Citation
A. Arcelli et al., Mechanistic investigation of an anomalous anchimeric assistance in the acid hydrolysis of the ether linkage. Part 4, TETRAHEDRON, 57(18), 2001, pp. 4039-4043
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
18
Year of publication
2001
Pages
4039 - 4043
Database
ISI
SICI code
0040-4020(20010430)57:18<4039:MIOAAA>2.0.ZU;2-X
Abstract
Kinetic investigation of the acid hydrolysis of N-(methoxyprop-2-yl)benzani lide (1) was performed in 8.84 M HCl and/or DCl at 75.1 degreesC. The forma tion of 2-(N-phenylamino)propanol (4) was explained and the mechanism, invo lving an initial ether cleavage anchimerically assisted by the amide group, was clarified. The overall process evolves through three steps involving t wo intermediates. The rate constants of the individual processes have been determined by UV and H NMR spectroscopic techniques. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.