Mechanism of the carbonyl-ene reaction

被引：11

作者：

Achmatowicz, O ^{[1
]}

BialeckaFlorjanczyk, E ^{[1
]}

机构：

[1] AGR UNIV WARSAW,PL-02528 WARSAW,POLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 26期

关键词：

D O I：

10.1016/0040-4020(96)00424-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The isolation of the ene adducts in the thermal reaction of allylbenzene and 3-phenyibut-1-ene with oxomalonic esters and cyclization or skeletal rearrangement products in the tin tetrachloride mediated addition has been interpreted as indicating a change of the mechanism from concerted (thermal) to an ionic one in the case of a catalyzed reaction. (C) 1996 Elsevier Science Ltd

引用

收藏

页码：8827 / 8834

页数：8

相关论文

共 11 条

[1] LEWIS ACID CATALYSIS OF THE ENE ADDITION OF DIMETHYL OXOMALONATE AND BUTYL GLYOXYLATE TO OLEFINS - FORMATION OF CYCLIC ETHERS AND LACTONES [J].

ACHMATOWICZ, O ;

ROZWADOWSKI, J ;

SZECHNER, B ;

SZYMONIAK, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (05) :1011-1018

[2] SCOPE AND MECHANISM OF THE REACTION OF OLEFINS WITH ANHYDRIDES AND ZINC-CHLORIDE TO GIVE BETA,GAMMA-UNSATURATED KETONES [J].

BEAK, P ;

BERGER, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3848-3856

[3] LEWIS ACID CATALYSIS OF THE ENE ADDITION OF CHLORAL AND BROMAL TO OLEFINS - PRODUCT STUDIES [J].

BENNER, JP ;

GILL, GB ;

PARROTT, SJ ;

WALLACE, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :291-313

[4] LEWIS ACID CATALYSIS OF THE ENE ADDITION OF CHLORAL AND BROMAL TO OLEFINS - STEREOCHEMICAL AND MECHANISTIC STUDIES [J].

BENNER, JP ;

GILL, GB ;

PARROTT, SJ ;

WALLACE, B ;

BEGLEY, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :315-329

[5]

BODEN RM, 1975, SYNTHESIS-STUTTGART, P784

[6] OBSERVATIONS ON THE MECHANISM OF THE LEWIS ACID-CATALYZED ENE REACTION [J].

KWART, H ;

BRECHBIEL, M .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5409-5411

[7] ASYMMETRIC ENE REACTIONS IN ORGANIC-SYNTHESIS [J].

MIKAMI, K ;

SHIMIZU, M .

CHEMICAL REVIEWS, 1992, 92 (05) :1021-1050

[8] DIETHYL OXOMALONATE - AN IMPROVED SYNTHESIS [J].

PARDO, SN ;

SALOMON, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2598-2599

[9]

Perrin D. D., 1988, PURIFICATION LAB CHE

[10] SELECTIVITY AND CATALYSIS IN ENE REACTIONS OF DIETHYL OXOMALONATE [J].

SALOMON, MF ;

PARDO, SN ;

SALOMON, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) :2446-2454