The vicarious nucleophilic substitution of hydrogen proceeding via a cyclopropane ring-opening

被引：3

作者：

Stalewski, J ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 51期

关键词：

cyclopropanes; carbanions; nitro compounds; substitution;

D O I：

10.1016/S0040-4039(98)02114-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Cyano-2,2-diethoxycarbonyl cyclopropane was reacted with several nitroarenes under basic conditions. The reaction proceeded according to the vicarious nucleophilic substitution of hydrogen scheme; i.e. the initially formed sigma-adducts underwent base-induced elimination, resulting in cleavage of the cyclopropane ring. The ortho-substituted products can be directly transformed into substituted N-hydroxyindoles. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9523 / 9526

页数：4

共 15 条

[1]

BOCHE G, 1990, CYCLOPROPANE DERIVED, P67

[2] ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS [J].

DANISHEFSKY, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (02) :66-72

[3] THE CONTRIBUTION OF RING STRAIN TO NUCLEOFUGALITY - THE 1ST MEASUREMENT [J].

GRIFFITHS, G ;

HUGHES, S ;

STIRLING, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (04) :236-237

[4] ELIMINATIVE CLEAVAGE OF CYCLOPROPANES - LEAVING GROUP STABILIZATION AND TRANSITION-STATE STRUCTURE [J].

HUGHES, S ;

STIRLING, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (04) :237-238

[5]

LEMENN JC, 1991, CAN J CHEM, V69, P761

[6] Vicarious nucleophilic substitution of hydrogen proceeding via heterocyclic ring opening [J].

Makosza, M ;

Sypniewski, M ;

Glinka, T .

TETRAHEDRON, 1996, 52 (09) :3189-3194

[7] OXIDATIVE VERSUS VICARIOUS NUCLEOPHILIC-SUBSTITUTION OF HYDROGEN IN THE REACTION OF DITHIANE DERIVATIVES WITH NITROARENES [J].

MAKOSZA, M ;

SYPNIEWSKI, M .

TETRAHEDRON, 1994, 50 (16) :4913-4920

[8] VICARIOUS NUCLEOPHILIC-SUBSTITUTION OF HYDROGEN [J].

MAKOSZA, M ;

WINIARSKI, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (08) :282-289

[9]

Makosza M, 1997, LIEBIGS ANN-RECL, P1805

[10]

MAKOSZA M, 1987, LIEBIGS ANN CHEM, P711

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