PROTONATION OF ACYLLITHIUM REAGENTS BY DICHLOROMETHANE AND DICHLOROARYLMETHANE - A NEW METHOD FOR THE SYNTHESIS OF ALPHA,ALPHA-DICHLORO ALCOHOLS

被引：17

作者：

KABALKA, GW ^{[1
]}

LI, NS ^{[1
]}

YU, S ^{[1
]}

机构：

[1] UNIV TENNESSEE,DEPT RADIOL,KNOXVILLE,TN 37996

来源：

ORGANOMETALLICS | 1995年 / 14卷 / 04期

关键词：

D O I：

10.1021/om00004a008

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first example of the protonation of acyl-lithium reagents by dichloromethane and dichloroarylmethane is described. The reaction affords the corresponding alpha,alpha-dichloro alcohols in excellent yields.

引用

页码：1565 / 1566

页数：2

共 23 条

[1]

DUHAMEL P, 1970, B SOC CHIM FR, P3641

[2] PRACTICAL PROCEDURE FOR THE PREPARATION OF HINDERED ALPHA-HALOEPOXIDES AND ALPHA-HALOALDEHYDES [J].

GRALAK, J ;

VALNOT, JY .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1979, 11 (3-4) :107-110

[3]

HUI RC, 1990, ORG SYNTH, V69, P114

[4] EVIDENCE FOR THE FORMATION OF ACYLBORONATE INTERMEDIATES IN THE CARBONYLATION REACTIONS OF ORGANOBORANES [J].

KABALKA, GW ;

GOTSICK, JT ;

PACE, RD ;

LI, NS .

ORGANOMETALLICS, 1994, 13 (12) :5163-5165

[5]

KIMPE ND, 1992, TETRAHEDRON, V48, P7345

[6]

NARAYANA C, 1985, SYNTHESIS-STUTTGART, P253

[7] ALPHA-HALOENOLATES - THEIR PREPARATION AND SYNTHETIC APPLICATIONS [J].

NORMANT, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 100 (01) :189-203

[8] CARBONYLATION OF ARYLLITHIUM REAGENTS IN THE PRESENCE OF ALKYL-HALIDES - ONE-POT SYNTHESIS OF DIARYLALKYLCARBINOLS AND DERIVATIVES [J].

NUDELMAN, NS ;

VITALE, AA .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) :4625-4626

[9] REACTIONS VIA CARBONYL ANIONS - [4+1] CYCLOCOUPLING OF THE AZADIENYLLITHIUM WITH CARBON-MONOXIDE [J].

ORITA, A ;

FUKUDOME, M ;

OHE, K ;

MURAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :477-481

[10] SYNTHESIS OF ALPHA-HYDROXY KETONES BY DIRECT, LOW-TEMPERATURE, INSITU NUCLEOPHILIC ACYLATION OF ALDEHYDES AND KETONES BY ACYLLITHIUM REAGENTS [J].

SEYFERTH, D ;

WEINSTEIN, RM ;

HUI, RC ;

WANG, WL ;

ARCHER, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5620-5629

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