LEWIS ACID CATALYSIS OF THE ENE ADDITION OF DIMETHYL OXOMALONATE AND BUTYL GLYOXYLATE TO OLEFINS - FORMATION OF CYCLIC ETHERS AND LACTONES

被引:2
作者
ACHMATOWICZ, O
ROZWADOWSKI, J
SZECHNER, B
SZYMONIAK, J
机构
关键词
D O I
10.1135/cccc19911011
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Lewis acid (SnCl4, TiCl4) catalyzed ene addition of dimethyl oxomalonate and butyl glyoxylate to pent-1-ene and 3-methylbut-1-ene has been investigated. Side reactions have been noted leading variously to the formation of delta-lactones and/or cyclic ethers (tetrahydrofurans). The effect on the reaction course of the structure of the substrates has been discussed.
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页码:1011 / 1018
页数:8
相关论文
共 21 条
[1]   KINETICS AND MECHANISM OF THE ENE REACTION OF DIMETHYL MESOXALATE WITH ALKENES [J].
ACHMATOWICZ, O ;
SZYMONIAK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (07) :1228-1232
[2]   PARTIAL ASYMMETRIC INDUCTION IN ENE REACTION [J].
ACHMATOWICZ, O ;
SZECHNER, B .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :964-+
[3]  
ACHMATOWICZ O, 1956, ROCZNIKI CHEM, V30, P215
[4]  
ACHMATOWICZ O, 1962, ROCZ CHEM, V35, P1791
[5]   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
[6]   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
[7]   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
[8]   MECHANISM OF THE (O --- H --- O) HYDROGEN TRANSFER IN ENE REACTIONS [J].
BENSALEM, R ;
JENNER, G .
TETRAHEDRON LETTERS, 1986, 27 (14) :1575-1576
[9]  
Conia JM, 1975, SYNTHESIS, V1
[10]  
HOFFMAN HMR, 1968, ANGEW CHEM INT EDIT, V8, P556