An expedient approach to allenes and polycyclic structures using propargyl radicals

被引：37

作者：

Alameda-Angulo, C ^{[1
]}

Quiclet-Sire, W ^{[1
]}

Zard, SZ ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Organ Synth Lab, F-91128 Palaiseau, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 06期

关键词：

D O I：

10.1016/j.tetlet.2005.11.154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach to the synthesis of allenes and polycyclic structures has been developed, based on the addition of a xanthate to an enyne followed by ring-closure of the allenyl radical on to an internal olefin. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：913 / 916

页数：4

共 22 条

[1] Spin delocalization by triple-bonded functionalities in propargyl and heteropropargyl radicals, assessed from the EPR-spectral D parameter of 1,3-cyclopentanediyl triplet diradicals [J].

Adam, W ;

Ortega-Schulte, CM .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1007-1011

[2] STEREOCHEMISTRY OF THE DIELS-ALDER REACTION OF BUTADIENE WITH CYCLOPROPENE [J].

BALDWIN, JE ;

REDDY, VP .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5264-5267

[3] Study of a radical cyclizations cascade leading to bicyclo[3.1.1]heptanes [J].

Bogen, S ;

Fensterbank, L ;

Malacria, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :819-825

[4] CYCLIZATION OF IMINE RADICALS DERIVED FROM SULPHENYLIMINES - A SIMPLE ACCESS TO DELTA-1-PYRROLINES [J].

BOIVIN, J ;

FOUQUET, E ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1990, 31 (01) :85-88

[5]

CASERIO MC, 1967, TETRAHEDRON LETT, P91

[6] FREE RADICALS BY MASS SPECTROMETRY .13. THE MERCURY PHOTOSENSITIZED DECOMPOSITION OF ALLENE AND BUTADIENE - THE C3H3 RADICAL [J].

COLLIN, J ;

LOSSING, FP .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1957, 35 (08) :778-787

[7]

Curran D. P., 1991, COMPREHENSIVE ORGANI, V4, P715

[8] CONVERSION OF THIOCARBONYL COMPOUNDS INTO THEIR CORRESPONDING OXODERIVATIVES USING BENZENESELENINIC ANHYDRIDE [J].

CUSSANS, NJ ;

LEY, SV ;

BARTON, DHR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (08) :1650-1653

[9] A synthetically useful source of propargyl radicals. [J].

Denieul, MP ;

QuicletSire, B ;

Zard, SZ .

TETRAHEDRON LETTERS, 1996, 37 (31) :5495-5498

[10] THERMOLYSIS OF PERESTERS - RELATIVE STABILITY OF ALLYLIC AND PROPARGYLIC RADICALS [J].

ENGEL, PS ;

DALTON, AI ;

SHEN, L .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (03) :384-388

← 1 2 3 →