Reaction of vinylcarbenoids with aldehydes: formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans

被引：17

作者：

Hamaguchi, M ^{[1
]}

Matsubara, H ^{[1
]}

Nagai, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Chem Mat, Toyonaka, Osaka 560, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 09期

关键词：

carbenes and carbenoids; carbonyl ylides; cyclization; diazo compounds;

D O I：

10.1016/S0040-4039(99)02317-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh-2(OAc)(4)-catalyzed reaction of vinyldiazo compound 1 in the presence of benzaldehydes 2a-2c gave a mixture of isomeric vinyloxiranes 3 and 4, and sterically unstable (E)-dihydrofurans 5, but not stable (Z)-dihydrofurans 6. However, the reaction in the presence of maleic anhydride gave single 1,3-dipolar cycloadducts 15, indicating that onyl endo-aryl-endo-cyanostyryl carbonyl ylide 7 (8) is initially formed in the reaction of 1 with 2. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1457 / 1460

页数：4

共 15 条

[1]

CHOU WN, 1991, TETRAHEDRON LETT, V32, P7627

[2] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[3] VINYLOXIRANE DIHYDROFURAN ISOMERIZATION - MECHANISM AND SYNTHETIC USE [J].

EBERBACH, W ;

BURCHARDT, B .

CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (11) :3665-3698

[4] SYNTHESIS, THERMOLYSIS, AND PHOTOLYSIS OF SUBSTITUTED 3,4-EPOXY-CYCLOALKENES [J].

EBERBACH, W ;

CARRE, JC .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (03) :1027-1047

[5]

EBERBACH W, 1977, TETRAHEDRON LETT, P3569

[6] THERMOLYSIS OF COMPOUNDS WITH A GEOMETRICALLY FIXED VINYLOXIRANE UNIT - STEREOSPECIFIC SYNTHESIS OF 4,5-FUSED CIS-2,3-DIHYDROFURANS AND TRANS-2,3-DIHYDROFURANS [J].

EBERBACH, W ;

SEILER, W ;

FRITZ, H .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (03) :875-901

[7]

EBERBACH W, 1976, TETRAHEDRON LETT, P3887

[8] CONFIGURATION INTERACTION AND ORGANIC REACTIVITY .2. ELECTROCYCLIC REACTIONS [J].

EPIOTIS, ND .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (04) :1200-1206

[9] ELECTRONIC STRUCTURE OF OPEN FORMS OF 3-MEMBERED RINGS [J].

HAYES, EF ;

SIU, AKQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (08) :2090-&

[10] ELECTROCYCLIC RING-OPENING REACTIONS OF ETHYLENE OXIDES [J].

HUISGEN, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (09) :572-585

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