PREPARATION OF METHYL CARBAMATES VIA A MODIFIED HOFMANN REARRANGEMENT

Authors
HUANG XC KEILLOR JW
Citation
Xc. Huang et Jw. Keillor, PREPARATION OF METHYL CARBAMATES VIA A MODIFIED HOFMANN REARRANGEMENT, Tetrahedron letters, 38(3), 1997, pp. 313-316
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
3
Year of publication
1997
Pages
313 - 316
Database
ISI
SICI code
0040-4039(1997)38:3<313:POMCVA>2.0.ZU;2-O
Abstract
Treatment of a series of para-substituted aromatic and primary aliphat ic carboxamides with NBS and NaOMe in methanol heated to reflux for te n minutes results in the conversion of the carboxamides to their corre sponding primary amino methyl carbamates in nearly quantitative yields . The mild oxidative conditions of this modified Hofmann rearrangement are shown to be particularly useful for the preparation of p-substitu ted anilines. Copyright (C) 1996 Elsevier Science Ltd