Synthesis of 2,3-disubstituted norbornadienes

被引：32

作者：

Tranmer, GK ^{[1
]}

Yip, C ^{[1
]}

Handerson, S ^{[1
]}

Jordan, RW ^{[1
]}

Tam, W ^{[1
]}

机构：

[1] Univ Guelph, Dept Chem & Biochem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Guelph, ON N1G 2W1, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2000年 / 78卷 / 05期

关键词：

2,3-disubstituted norbornadienes; Diels-Alder reaction; lithium halide exchange;

D O I：

10.1139/cjc-78-5-527

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Various 2,3-disubstituted norbornadienes that can hardly be made by the traditional Diels-Alder method were synthesized by double lithium halide exchange of 2,3-dibromonorbornadiene in moderate to good yields.

引用

页码：527 / 535

页数：9

共 27 条

[1] THE SYNTHESIS OF NORBORNADIENES CONJUGATIVELY LINKED TO TETRAPHENYLPORPHYRIN AND ANTHRACENE - TOWARDS A NORBORNADIENE-DERIVED MOLECULAR ELECTRONIC DEVICE [J].

BONFANTINI, EE ;

OFFICER, DL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (12) :1445-1446

[2] Photoinitiated rearrangements of 3-phenylnorbornadiene with conjugated substituents in 2-position [J].

Chernoivanov, VA ;

Dubonosov, AD ;

Bren, VA ;

Minkin, VI ;

Suslov, AN ;

Borodkin, GS .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1997, 297 :239-245

[3]

COREY EJ, 1976, TETRAHEDRON LETT, P737

[4] Enantioselective Diels-Alder reactions between cyclopentadiene and alpha,beta-acetylenic aldehydes catalyzed by a chiral super Lewis acid [J].

Corey, EJ ;

Lee, TW .

TETRAHEDRON LETTERS, 1997, 38 (33) :5755-5758

[5] PHOTOCHEMICAL TRANSFORMATIONS .8. ISOMERIZATION DELTA 2,5-BICYCLO [2.2.1] HEPTADIENE TO QUADRICYCLO[2.2.1.02,6O3,5]HEPTANE (QUADRICYCLENE) [J].

DAUBEN, WG ;

CARGILL, RL .

TETRAHEDRON, 1961, 15 (1-4) :197-&

[6]

Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01

[7]

GASSMAN PG, 1980, J AM CHEM SOC, V102, P6864

[8] PHOTOSENSITIZED CYCLOADDITION REACTIONS [J].

HAMMOND, GS ;

TURRO, NJ ;

FISCHER, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (22) :4674-&

[9]

HECK RF, 1991, COMPREHENSIVE ORGANI, V4, P883

[10]

HOLMES HL, 1948, ORG REACTIONS, V4, P60

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