VICARIOUS NUCLEOPHILIC AROMATIC-SUBSTITUTION VIA TRAPPING OF AN ALPHA-KETOSULFONIUM ION GENERATED BY PUMMERER-TYPE REARRANGEMENT OF 2-(PHENYLSULFINYL)PHENOLS - PREPARATION OF BIARYLS

被引：29

作者：

JUNG, ME

KIM, C

VONDEMBUSSCHE, L

机构：

[1] Department of Chemistry Biochemistry, University of California, Los Angeles

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 12期

关键词：

D O I：

10.1021/jo00091a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the nucleophilic substitution of phenols at the ortho position has been developed which uses as the key step the trapping of an alpha-ketosulfonium salt generated by a Pummerer rearrangement of 2-(phenylsulfinyl)phenols. In addition to preparing 2-halo- and 2-(acyloxy)phenols, this ''vicarious substitution'' also allows the preparation of biaryls in fair yield.

引用

收藏

页码：3248 / 3249

页数：2

相关论文

共 11 条

[1] TOTAL SYNTHESIS OF L,L-ISODITYROSINE AND ISODITYROSINE-DERIVED AGENTS - K-13, OF4949-III, AND OF4949-IV [J].

BOGER, DL ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) :6000-6017

[2]

CHASAR OW, 1978, PHOSPHORUS SULFUR, V5, P35

[3] THE TOTAL SYNTHESES OF THE ISODITYROSINE-DERIVED CYCLIC TRIPEPTIDES OF4949-III AND K-13 - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF K-13 [J].

EVANS, DA ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1063-1072

[4] FACILE CHEMICAL SYNTHESIS OF S,S-ISODITYROSINE, A NATURALLY-OCCURRING CROSS-LINKING AMINO-ACID [J].

JUNG, ME ;

JACHIET, D ;

ROHLOFF, JC .

TETRAHEDRON LETTERS, 1989, 30 (32) :4211-4214

[5] ORGANIC-CHEMISTRY OF L-TYROSINE .1. GENERAL-SYNTHESIS OF CHIRAL PIPERAZINES FROM AMINO-ACIDS [J].

JUNG, ME ;

ROHLOFF, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4909-4913

[6]

JUNG MYL, UNPUB

[7] HOST-GUEST COMPLEXATION .16. SYNTHESIS AND CATION BINDING CHARACTERISTICS OF MACROCYCLIC POLYETHERS CONTAINING CONVERGENT METHOXYARYL GROUPS [J].

KOENIG, KE ;

LEIN, GM ;

STUCKLER, P ;

KANEDA, T ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) :3553-3566

[8] SYNTHESIS OF PIPERAZINOMYCIN, A NOVEL ANTIFUNGAL ANTIBIOTIC [J].

NISHIYAMA, S ;

NAKAMURA, K ;

SUZUKI, Y ;

YAMAMURA, S .

TETRAHEDRON LETTERS, 1986, 27 (37) :4481-4484

[9]

NORRIS RK, 1991, COMPREHENSIVE ORGANI, V4, P469

[10]

PUMMERER OR, 1925, CHEM BER, V58, P1808