TORQUOSELECTIVITY IN THERMAL ELECTROCYCLIC REACTIONS OF SUBSTITUTED 7-(ETHOXYCARBONYL)BICYCLO[4.2.0]OCT-1(6)-ENES

被引：15

作者：

PIERS, E

ELLIS, KA

机构：

[1] Department of Chemistry, University of British Columbia, Vancouver, BC V6T 1Z1

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)91951-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the thermally induced electrocyclic ring opening of the bicyclic esters 4-16, the ratio of products resulting from outward and inward rotation of the CO2Et group varies from 17:1 (substrate 10) to 1:2.6 (substrate 9).

引用

页码：1875 / 1878

页数：4

共 13 条

[1] THERMAL ELECTROCYCLIC RING-OPENING OF CYCLOBUTENES - STEREOSELECTIVE ROUTES TO FUNCTIONALIZED CONJUGATED (Z,E)-DIENES AND (E,E)-2,4-DIENALS [J].

BINNS, F ;

HAYES, R ;

INGHAM, S ;

SAENGCHANTARA, ST ;

TURNER, RW ;

WALLACE, TW .

TETRAHEDRON, 1992, 48 (03) :515-530

[2] ACID-BASE CONTROLLED TORQUOSELECTIVITY - THEORETICAL PREDICTIONS OF THE STEREOCHEMICAL COURSE OF THE ELECTROCYCLIC REACTIONS OF CYCLOBUTENE-3-CARBOXYLIC ACID AND THE CONJUGATE BASE AND ACID [J].

BUDA, AB ;

WANG, Y ;

HOUK, KN .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2264-2266

[3] CYCLOBUTENE RING-OPENING - A USEFUL REACTION FOR THE SYNTHESIS OF DOUBLE-STRANDED MOLECULES [J].

GODT, A ;

SCHLUTER, AD .

CHEMISCHE BERICHTE, 1991, 124 (01) :149-156

[4] ELECTRONIC CONTROL OF THE STEREOSELECTIVITIES OF ELECTROCYCLIC REACTIONS OF CYCLOBUTENES AGAINST INCREDIBLE STERIC ODDS [J].

HOUK, KN ;

SPELLMEYER, DC ;

JEFFORD, CW ;

RIMBAULT, CG ;

WANG, Y ;

MILLER, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :2125-2127

[5] TORQUOSELECTIVITY IN THE ELECTROCYCLIC CONVERSION OF BENZOCYCLOBUTENES TO ORTHO-XYLYLENES [J].

JEFFORD, CW ;

BERNARDINELLI, G ;

WANG, Y ;

SPELLMEYER, DC ;

BUDA, A ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1157-1165

[6] ELECTROCYCLIC RING OPENINGS OF DIALKYLCYCLOBUTENES - ANOMALIES EXPLAINED [J].

KALLEL, EA ;

YING, W ;

SPELLMEYER, DC ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :6759-6763

[7] COMPETITION BETWEEN ESTER AND FORMYL GROUPS FOR CONTROL OF TORQUOSELECTIVITY IN CYCLOBUTENE ELECTROCYCLIC REACTIONS [J].

NIWAYAMA, S ;

HOUK, KN .

TETRAHEDRON LETTERS, 1992, 33 (07) :883-886

[8] USE OF LITHIUM (TRIMETHYLSTANNYL)(CYANO)CUPRATE FOR THE CONVERSION OF ALKYL 2-ALKYNOATES INTO ALKYL (Z)-3-TRIMETHYLSTANNYL-2-ALKENOATES AND (E)-3-TRIMETHYLSTANNYL-2-ALKENOATES [J].

PIERS, E ;

WONG, T ;

ELLIS, KA .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (07) :2058-2064

[9] STEREOCHEMISTRY OF THERMAL RING-OPENING OF SUBSTITUTED 7-(ETHOXYCARBONYL)BICYCLO[4.2.0]OCT-1(6)-ENES AND RELATED SUBSTANCES [J].

PIERS, E ;

LU, YF .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2267-2268

[10] STEREOSPECIFIC DECONJUGATION OF ALKYL (E) AND (Z)-3-TRIMETHYLSTANNYL-2-ALKENOATES [J].

PIERS, E ;

GAVAI, AV .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2374-2379

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