FACIAL (SYN-ANTI) STEREOSELECTIVITY IN THE DIELS-ALDER REACTIONS OF SPIRO(BICYCLO[2.2.2]OCTANE-2,1'[2,4]CYCLOPENTADIENE)

被引：21

作者：

BURNELL, DJ ^{[1
]}

GOODBRAND, HB ^{[1
]}

KAISER, SM ^{[1
]}

VALENTA, Z ^{[1
]}

机构：

[1] UNIV NEW BRUNSWICK, DEPT CHEM, BAG SERVICE 45222, FREDERICTON E3B 6E2, NB, CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY | 1987年 / 65卷 / 01期

关键词：

D O I：

10.1139/v87-024

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Spiro(bicyclo[2.2.2]octane-2,1''-[2,4]cyclopentadiene) (3) has been synthesized in ten steps, and its Diel-Alder cycloadditions, both thermal and catalysed, have been studied with a variety of Z-ethylenic dienophiles. No significant differences in facial stereoselectivity were observed. This suggests that, in the exo region, the distance between the addends at the transition state is approximately the same in all the cases studied.

引用

页码：154 / 165

页数：12

共 65 条

[1]

Albrecht W., 1906, LIEBIGS ANN CHEM, V348, P31

[2] THE STEREOCHEMISTRY AND REGIOCHEMISTRY OF THE DIELS-ALDER REACTIONS OF 6-ACETOXY-2,6-DIMETHYL-2,4-CYCLOHEXADIENONE [J].

AUKSI, H ;

YATES, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (16) :2510-2517

[3] STEREOSELECTIVITY OF THE DIELS-ALDER ADDITIONS OF EXOCYCLIC DIENES GRAFTED ONTO BICYCLO[2.2.NORMAL]ALKANES [J].

AVENATI, M ;

HAGENBUCH, JP ;

MAHAIM, C ;

VOGEL, P .

TETRAHEDRON LETTERS, 1980, 21 (33) :3167-3170

[4] INTERACTIONS BETWEEN NON-CONJUGATED CHROMOPHORES .13. INTERACTION BETWEEN EXOCYCLIC S-CIS-BUTADIENE AND HOMOCONJUGATED FUNCTIONS - PREPARATION AND DIELS-ALDER REACTIVITY OF REMOTELY SUBSTITUTED 2,3-DIMETHYLIDENEBICYCLO[2.2.2]OCTANES [J].

AVENATI, M ;

PILET, O ;

CARRUPT, PA ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1982, 65 (01) :178-187

[5] INTERACTION BETWEEN NON-CONJUGATED CHROMOPHORES .15. FACE SELECTIVITY OF THE DIELS-ALDER ADDITIONS OF 2-SUBSTITUTED 5,6-BIS((E)-CHLOROMETHYLIDENE)BICYCLO[2.2.2]OCTANES [J].

AVENATI, M ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1982, 65 (01) :204-216

[6] INTERACTION BETWEEN NON-CONJUGATED CHROMOPHORES .14. REGIOSELECTIVITY OF THE DIELS-ALDER ADDITIONS OF 2-SUBSTITUTED 5,6-DIMETHYLIDENENORBORNANES AND DIMETHYLIDENEBICYCLO[2.2.2]OCTANES [J].

AVENATI, M ;

CARRUPT, PA ;

QUARROZ, D ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1982, 65 (01) :188-203

[7] REINTERPRETATION OF BETA-SUBSTITUENT, GAMMA-SUBSTITUENT, AND DELTA-SUBSTITUENT EFFECTS ON C-13 CHEMICAL-SHIFTS [J].

BEIERBECK, H ;

SAUNDERS, JK .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (19) :2985-2995

[8] THERMAL, NONCATALYTIC CYCLOADDITIONS OF ACRYL COMPOUNDS ON CYCLOHEPTATRIENE [J].

BELLUS, D ;

HELFERIC.G ;

WEIS, CD .

HELVETICA CHIMICA ACTA, 1971, 54 (02) :463-&

[9] THE STO-3G TRANSITION STRUCTURE OF THE DIELS-ALDER REACTION [J].

BROWN, FK ;

HOUK, KN .

TETRAHEDRON LETTERS, 1984, 25 (41) :4609-4612

[10] RELATIVE RATES OF ADDITION OF CYANO-ETHYLENES TO ANTHRACENE AND ITS 9-DEUTERIO- AND 9,10-DIDEUTERIO-DERIVATIVES [J].

BROWN, P ;

COOKSON, RC .

TETRAHEDRON, 1965, 21 (08) :1993-&

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