Novel intramolecular rearrangement of 3-bromo-3,3-difluoroalanine Schiff bases via radical ipso-substitution at the aromatic ring

被引：37

作者：

Amii, H ^{[1
]}

Kondo, S ^{[1
]}

Uneyama, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7000082, Japan

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 17期

关键词：

D O I：

10.1039/a803944e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3-Bromo-3,3-difluoroalanine Schiff bases are synthesized by bromodifluoromethylation of the corresponding glycine Schiff bases with CF2Br2; their intramolecular rearrangement involving radical ipso-substitution at the aromatic ring of the imine moiety provides 3,3-difluoro-3-arylpropanoates in good yields.

引用

页码：1845 / 1846

页数：2

共 12 条

[1] NEW COPPER(I)-CATALYZED REACTIONS OF OXAZIRIDINES - STEREOCHEMICAL CONTROL OF PRODUCT DISTRIBUTION [J].

AUBE, J ;

PENG, X ;

WANG, YG ;

TAKUSAGAWA, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5466-5467

[2]

BAY P, 1978, TETRAHEDRON LETT, V14, P1215

[3] INTRA-MOLECULAR AROMATIC IPSO-SUBSTITUTION IN THE PHOTOLYSIS OF 2-IODOAZOBENZENES [J].

BENATI, L ;

SPAGNOLO, P ;

TUNDO, A ;

ZANARDI, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (03) :141-143

[4] Observations on the nature of the tethering chain in the synthesis of biaryls and heterobiaryls via intramolecular free radical ipso substitution reactions. [J].

daMata, MLEN ;

Motherwell, WB ;

Ujjainwalla, F .

TETRAHEDRON LETTERS, 1997, 38 (01) :141-144

[5] Steric and electronic effects in the synthesis of biaryls and their heterocyclic congeners using intramolecular free radical [1,5] ipso substitution reactions. [J].

daMata, MLEN ;

Motherwell, WB ;

Ujjainwalla, F .

TETRAHEDRON LETTERS, 1997, 38 (01) :137-140

[6] ELECTROCHEMICAL REACTIONS .24. REDUCTIVE CYCLIZATION OF I-(2-HALOGENOPHENYL)-J-PHENYL COMPOUNDS - A GENERAL REACTION [J].

GRIMSHAW, J ;

HAMILTON, R ;

TROCHAGRIMSHAW, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :229-234

[7]

Kukhar VP., 1995, FLUORINE CONTAINING

[8] RADICAL ISOMERIZATION VIA INTRAMOLECULAR IPSO SUBSTITUTION OF N-ARYLAMIDES - ARYL TRANSLOCATION FROM NITROGEN TO CARBON [J].

LEE, E ;

WHANG, HS ;

CHUNG, CK .

TETRAHEDRON LETTERS, 1995, 36 (06) :913-914

[9] A MILD AND EFFICIENT ROUTE TO SCHIFF-BASE DERIVATIVES OF AMINO-ACIDS [J].

ODONNELL, MJ ;

POLT, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2663-2666

[10] [3,3]-SIGMATROPIC REARRANGEMENT ROUTES TO BETA-FLUORO-CARBONYL AND BETA,BETA-DIFLUORO-CARBONYL DERIVATIVES [J].

PATEL, ST ;

PERCY, JM ;

WILKES, RD .

TETRAHEDRON, 1995, 51 (41) :11327-11336

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