Preparation of methyl carbamates via a modified Hofmann rearrangement

被引：46

作者：

Huang, XC ^{[1
]}

Keillor, JW ^{[1
]}

机构：

[1] UNIV MONTREAL,DEPT CHIM,MONTREAL,PQ H3C 1J7,CANADA

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(96)02341-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of a series of para-substituted aromatic and primary aliphatic carboxamides with NBS and NaOMe in methanol heated to reflux for ten minutes results in the conversion of the carboxamides to their corresponding 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-substituted anilines. Copyright (C) 1996 Elsevier Science Ltd

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页码：313 / 316

页数：4

相关论文

共 11 条

[1] REACTIONS OF AMINES .18. OXIDATIVE REARRANGEMENT OF AMIDES WITH LEAD-TETRAACETATE [J].

BAUMGARTEN, HE ;

SMITH, HL ;

STAKLIS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (24) :3554-3561

[2]

De la Saulnilre PC, 1942, ANN CHIM FRANCE, V17, P353

[3] INTERMOLECULAR REACTIONS OF N-ALKOXYCARBONYLIMINIUM IONS WITH PROPARGYLTRIMETHYLSILANE - OXAZINONE VERSUS ALLENE FORMATION [J].

ESCH, PM ;

HIEMSTRA, H ;

SPECKAMP, WN .

TETRAHEDRON, 1992, 48 (16) :3445-3462

[4] HALOGENATION USING QUATERNARY AMMONIUM POLYHALIDES .9. ONE-STEP SYNTHESES OF ACYLUREAS AND CARBAMATES FROM AMIDES BY USE OF TETRABUTYLAMMONIUM TRIBROMIDE AND DBU [J].

FUJISAKI, S ;

TOMIYASU, K ;

NISHIDA, A ;

KAJIGAESHI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (04) :1401-1403

[5] NEW METHOD FOR HOFMANN REARRANGEMENT [J].

JEW, SS ;

PARK, HG ;

PARK, HJ ;

PARK, MS ;

CHO, YS .

TETRAHEDRON LETTERS, 1990, 31 (11) :1559-1562

[6] OXIDATION USING QUATERNARY AMMONIUM POLYHALIDES .1. AN EFFICIENT METHOD FOR THE HOFMANN DEGRADATION OF AMIDES BY USE OF BENZYLTRIMETHYLAMMONIUM TRIBROMIDE [J].

KAJIGAESHI, S ;

ASANO, K ;

FUJISAKI, S ;

KAKINAMI, T ;

OKAMOTO, T .

CHEMISTRY LETTERS, 1989, (03) :463-464

[7] PREPARATION OF METHYL CARBAMATES FROM PRIMARY ALKYLCARBOXAMIDES AND ARYLCARBOXAMIDES USING HYPERVALENT IODINE [J].

MORIARTY, RM ;

CHANY, CJ ;

VAID, RK ;

PRAKASH, O ;

TULADHAR, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2478-2482

[8]

RADLICK P, 1974, SYNTHESIS-STUTTGART, P290

[9] NATURE OF N-BROMOSUCCINIMIDE IN BASIC-MEDIA - THE TRUE OXIDIZING SPECIES IN THE HOFMANN REARRANGEMENT [J].

SENANAYAKE, CH ;

FREDENBURGH, LE ;

REAMER, RA ;

LARSEN, RD ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7947-7948

[10] QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIPS OF THE FUNGICIDAL METHYL N-PHENYLCARBAMATES [J].

TAKAHASHI, J ;

KIRINO, O ;

TAKAYAMA, C ;

NAKAMURA, S ;

NOGUCHI, H ;

KATO, T ;

KAMOSHITA, K .

PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 1988, 30 (03) :262-271