INTRAMOLECULAR CYCLOADDITIONS OF METHYLENECYCLOPROPANES - A NOVEL CHELATION EFFECT

被引：41

作者：

MOTHERWELL, WB

SHIPMAN, M

机构：

[1] Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(00)74499-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to the palladium catalysed reactions of methylenecyclopropane (1), cyclisation of methylenecyclopropane (7) yields trans fused bicyclo[3.3.0]octanes (8) and (9). Intramolecular chelation by an appended ether unit is proposed to account for the observed selectivities.

引用

页码：1103 / 1106

页数：4

共 7 条

[1] BAPUJI SA, 1989, TETRAHEDRON LETT, V30, P7107
[2] 5-ALKYLIDENE-HEXAHYDRO-1H-CYCLOPENTA[C]PYRROL-1,3-DIONES BY NICKEL(0) OR PALLADIUM(0) CATALYZED [3+2] CYCLO-ADDITION OF METHYLENECYCLOPROPANES WITH MALEIMIDES
BINGER, P
FREUND, A
WEDEMANN, P
[J]. TETRAHEDRON, 1989, 45 (10) : 2887 - 2894
[3] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
CRAIG, D
[J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238
[4] OBSERVATIONS ON THE INTRAMOLECULAR PALLADIUM(0) CATALYZED [3 + 2] CYCLO-ADDITION OF DIPHENYLMETHYLENECYCLOPROPANES
LEWIS, RT
MOTHERWELL, WB
SHIPMAN, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) : 948 - 950
[5] INTRAMOLECULAR CARBOCYCLIC [3+2] CYCLOADDITION VIA ORGANOPALLADIUM INTERMEDIATES
TROST, BM
CHAN, DMT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3733 - 3735
[6] [3+2] CYCLOADDITION APPROACHES TO 5-MEMBERED RINGS VIA TRIMETHYLENEMETHANE AND ITS EQUIVALENTS
TROST, BM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (01): : 1 - 20
[7] SYNTHESIS OF PROPELLANES BY EXOCYCLIC TRANS-ANNULAR CYCLO-ADDITION OF OLEFINIC METHYLENECYCLOPROPANES
YAMAGO, S
NAKAMURA, E
[J]. TETRAHEDRON, 1989, 45 (10) : 3081 - 3088

← 1 →