Effect of solvent polarity extremes on the coupling of cyclopropylcarbene-chromium complexes and alkynes: Synthesis of beta-alkoxycyclopentadienones, 2-cyclopentene-1,3-diones, and cis 4,5-disubstituted cyclopentenones

被引：27

作者：

Herndon, JW

Patel, PP

机构：

[1] Department of Chemistry, University of Maryland, College Park

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 01期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(96)02282-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between acetylenes and cyclopropylcarbene-chromium complexes in hexane affords exclusively cyclopentadienone derivatives in good yield, which are readily hydrolyzed to cyclopentenediones. The analogous reaction in 50:50 water dioxane affords cis disubstituted cyclopentenones. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：59 / 62

页数：4

相关论文

共 16 条

[1] REDUCTION REACTIONS OF ORGANOMETALLIC COMPOUNDS .1. [J].

BROWN, DA ;

HARGADEN, JP ;

MCMULLIN, CM ;

SLOAN, H ;

GOGAN, N .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (OCT) :4914-&

[2] THE CHEMISTRY OF TETRAKIS(TRIFLUOROMETHYL)CYCLOPENTADIENONE [J].

BURK, MJ ;

CALABRESE, JC ;

DAVIDSON, F ;

HARLOW, RL ;

ROE, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2209-2222

[3]

FOX MA, 1983, J ORG CHEM, V48, P381

[4] CYCLOPENTADIENONES IN THE REACTION OF ALKYNES WITH CYCLOPROPYLCARBENE-CHROMIUM COMPLEXES [J].

HERNDON, JW ;

TUMER, SU .

TETRAHEDRON LETTERS, 1989, 30 (03) :295-296

[5] SYNTHESIS OF CYCLOPENTANE-FUSED OXYGEN HETEROCYCLES FROM THE INTRAMOLECULAR REACTION OF ALKYNES WITH CYCLOPROPYLCARBENE CHROMIUM COMPLEXES [J].

HERNDON, JW ;

MATASI, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :786-788

[6]

HERNDON JW, 1994, ADV MET ORG, V0003, P00051

[7]

HERNDON JW, 1988, J AM CHEM SOC, V10, P3334

[8] A NEW APPROACH TO RETHROLONE SYNTHESIS [J].

JONDIKO, IJO ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (02) :467-469

[9]

KAPILOV J, 1990, J ELECTROANAL CHEM, V280, P381

[10] ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION [J].

LI, CJ .

CHEMICAL REVIEWS, 1993, 93 (06) :2023-2035