CLEAVAGE OF 2,3-EPOXYALKYLHALIDES BY THE SONOCHEMICAL ZINC COPPER COUPLE

被引：39

作者：

SARANDESES, LA

MOURINO, A

LUCHE, JL

机构：

[1] UNIV GRENOBLE 1,LEDSS,BP 53X,F-38041 GRENOBLE,FRANCE

[2] UNIV SANTIAGO,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 12期

关键词：

D O I：

10.1039/c39910000818

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,3-Epoxyalkylhalides are readily transformed into allylic alcohols when sonicated in the presence of a zinc-copper couple in aqueous ethanol.

引用

页码：818 / 820

页数：3

共 12 条

[1] RADICAL-INDUCED RING-OPENING OF EPOXIDES - A CONVENIENT ALTERNATIVE TO THE WHARTON REARRANGEMENT [J].

BARTON, DHR ;

MOTHERWELL, RSH ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08) :2363-2367

[2] A NOVEL PROBE FOR FREE-RADICALS FEATURING EPOXIDE CLEAVAGE [J].

DICKINSON, JM ;

MURPHY, JA ;

PATTERSON, CW ;

WOOSTER, NF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :1179-1184

[3] TELLURIDE-MEDIATED STEREOSPECIFIC CONVERSION OF RACEMIC E-ALLYLIC ALCOHOLS TO HOMOCHIRAL Z-ALLYLIC ALCOHOLS - TRANSPOSITION OF PRIMARY AND SECONDARY ALLYLIC ALCOHOLS VIA GLYCIDOL DERIVATIVES [J].

DISCORDIA, RP ;

MURPHY, CK ;

DITTMER, DC .

TETRAHEDRON LETTERS, 1990, 31 (39) :5603-5606

[4]

DUPUY C, 1991, IN PRESS SYNTH COMMU, V21

[5]

FIESER LF, 1967, REAGENTS ORGANIC SYN, V1, P1292

[6] FREE-RADICAL CYCLIZATION OF UNSATURATED EPOXIDES [J].

GASH, RC ;

MACCORQUODALE, F ;

WALTON, JC .

TETRAHEDRON, 1989, 45 (17) :5531-5538

[7] CYCLIZATIONS OF ALLYLOXY RADICALS [J].

JOHNS, A ;

MURPHY, JA .

TETRAHEDRON LETTERS, 1988, 29 (07) :837-840

[8] TETRAKIS[IODO(TRI-NORMAL-BUTYLPHOSPHINE)-COPPER(I)] AND IODO-(2,2'-BIPYRIDINE)-(TRI-NORMAL-BUTYLPHOSPHINE)COPPER(I) [J].

KAUFFMAN, GB ;

TETER, LA .

INORGANIC SYNTHESES, 1963, 7 :9-12

[9] REACTIONS OF 2,3-EPOXYHALIDES - SYNTHESIS OF OPTICALLY-ACTIVE ALLYLIC ALCOHOLS AND HOMOALLYLIC EPOXIDES [J].

NICOLAOU, KC ;

DUGGAN, ME ;

LADDUWAHETTY, T .

TETRAHEDRON LETTERS, 1984, 25 (20) :2069-2072

[10] SYNTHESIS OF CARBOCYCLIC SYSTEMS VIA RADICAL-INDUCED EPOXIDE FRAGMENTATION [J].

RAWAL, VH ;

NEWTON, RC ;

KRISHNAMURTHY, V .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5181-5183

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