A TRANSANNULAR PI-BOND PAIRING APPROACH TO THE SYNTHESIS OF 1,3-CYCLOPENTADIENE DIESTERS AND MALEIMIDO-OXEPINES AND A REPORT ON THEIR ISOMERIZATION

被引：9

作者：

WARRENER, RN ^{[1
]}

BINA, S ^{[1
]}

BUTLER, DN ^{[1
]}

PITT, IG ^{[1
]}

RUSSELL, RA ^{[1
]}

机构：

[1] YORK UNIV,DEPT CHEM,N YORK M3J 1P3,ONTARIO,CANADA

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(00)97246-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polycyclobutanoid compounds containing an end-fused 3-membered ring are central to the synthesis of the title target molecules: a new mode for their production is presented. Cyclopentadiene 1,3-diester is isolated and its isomerisation studied. Intermediates supporting the oxygen-walk isomerisation of maleimido-oxepines are isolated. © 1990.

引用

收藏

页码：7073 / 7076

页数：4

相关论文

共 12 条

[1]

AZZENA U, 1989, GAZZ CHIM ITAL, V119, P357

[2] PREPARATION OF OXEPINES DURING DIRECT CHEMICAL SYNTHESIS AND FACILE OXYGEN WALK REACTIONS OF ARENE OXIDES - THEORETICAL PREDICTIONS AND EXPERIMENTAL-EVIDENCE [J].

BOYD, DR ;

AGARWAL, SK ;

BALANI, SK ;

DUNLOP, R ;

GADAGINAMATH, GS ;

OKANE, GA ;

SHARMA, ND ;

JENNINGS, WB ;

YAGI, H ;

JERINA, DM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1633-1635

[3] BICYCLO[2.1.0]PENT-2-ENE [J].

BRAUMAN, JI ;

ELLIS, LE ;

VAN TAMELEN, EE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (04) :846-+

[4]

Butler D.C.D., UNPUB

[5] PINCHING GROUP STABILIZATION - THE SYNTHESIS AND THERMAL-ISOMERIZATION OF 10-OXAPENTACYCLO[6.3.2.13,6.01,8.02,7]TETRADECA-4,12-DIENE [J].

BUTLER, DN ;

RUSSELL, RA ;

WARING, RB ;

WARRENER, RN .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (06) :1293-1302

[6] THE ARENE OXIDE-OXEPINE VALENCE ISOMERIZATION - A DYNAMIC NMR INVESTIGATION USING A PROCHIRAL SUBSTITUENT [J].

JENNINGS, WB ;

RUTHERFORD, M ;

BOYD, DR ;

AGARWAL, SK ;

SHARMA, ND .

TETRAHEDRON, 1988, 44 (24) :7551-7558

[7]

KOSTER JB, 1971, SYNTH-INT J METHODS, P139

[8] SYNTHESIS AND FRAGMENTATION REACTIONS OF CYCLIC AZO-COMPOUNDS - STEREOCHEMISTRY AND TRANSFORMATIONS OF PHOTO-DERIVED BICYCLO[2,1,0]-PENTANES, AND THERMAL CYCLOREVERSION REACTIONS OF TRICYCLO[6,2,1,02,7]- UNDECATRIENES AND RELATED COMPOUNDS [J].

LAY, WP ;

MACKENZI.K ;

TELFORD, JR .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (19) :3199-+

[9] RUTHENIUM-CATALYZED [2+2] CROSS-ADDITION OF NORBORNENE DERIVATIVES AND DIMETHYL ACETYLENEDICARBOXYLATE [J].

MITSUDO, T ;

KOKURYO, K ;

SHINSUGI, T ;

NAKAGAWA, Y ;

WATANABE, Y ;

TAKEGAMI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4492-4495

[10]

SMITH CD, 1966, J AM CHEM SOC, V107, P3287