Nitrosocarbonyl intermediates as "super-enophiles": A mild method for carbon-nitrogen bond formation

被引：39

作者：

Quadrelli, P ^{[1
]}

Mella, M ^{[1
]}

Caramella, P ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 20期

关键词：

cycloadditions; ene reactions; nitrile oxides; nitroso compounds;

D O I：

10.1016/S0040-4039(98)00399-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrosocarbonyl intermediates, generated at r.t. by the mild oxidation of nitrile oxides, undergo clean ene reactions with tetramethyl-and trimethyl-ethylene and with cyclohexene. With less substituted ethylenes the ene pathway is still active but the oxidation step of the nitrile oxides competes with the cycloadditions to the olefins. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3233 / 3236

页数：4

共 13 条

[1] 1,3-DIPOLAR CYCLOADDITIONS .73. RELATIVE DIPOLAROPHILE ACTIVITIES IN CYCLOADDITIONS OF BENZONITRILE OXIDE
BAST, K
CHRISTL, M
HUISGEN, R
MACK, W
[J]. CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (10): : 3312 - 3344
[2] Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, V1, P291
[3] The nature of the transition structures of triazolinedione ene reactions
Chen, JS
Houk, KN
Foote, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) : 9852 - 9855
[4] C-NITROSOFORMAMIDES, A NEW CLASS OF TRANSIENT DIENOPHILES FORMED BY OXIDATION OF N-HYDROXYUREAS
CHRISTIE, CC
KIRBY, GW
MCGUIGAN, H
MACKINNON, JWM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2469 - 2473
[5] CJENG CC, 1984, J ORG CHEM, V49, P2910
[6] REACTIONS OF TRANSIENT-C-NITROSOCARBONYL COMPOUNDS WITH DIENES, MONOOLEFINS, AND NUCLEOPHILES
CORRIE, JET
KIRBY, GW
MACKINNON, JWM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04): : 883 - 886
[7] ORBITAL INTERACTION IN 3 SYSTEMS
INAGAKI, S
FUJIMOTO, H
FUKUI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (16) : 4693 - 4701
[8] A VERSATILE METHOD FOR CARBON-NITROGEN BOND FORMATION VIA ENE REACTIONS OF ACYLNITROSO COMPOUNDS
KECK, GE
WEBB, RR
YATES, JB
[J]. TETRAHEDRON, 1981, 37 (23) : 4007 - 4016
[9] NITROSOCARBONYL COMPOUNDS AS INTERMEDIATES IN OXIDATIVE CLEAVAGE OF HYDROXAMIC ACIDS
KIRBY, GW
SWEENY, JG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (19) : 704 - 705
[10] INTRAMOLECULAR ENE REACTIONS OF TRANSIENT, ALLYLIC, AND HOMOALLYLIC C-NITROSOFORMATE ESTERS
KIRBY, GW
MCGUIGAN, H
MCLEAN, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (09): : 1961 - 1966

← 1 2 →