N-(trans-1-Propenyl)carbazole:: an excellent dienophile for cation radical Diels-Alder cycloadditions

被引：10
|
作者：
Gao, DX [1 ]
Bauld, NL [1 ]
机构：
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 32期
基金：
美国国家科学基金会;
关键词：
cycloaddition; Diels-Alder; propenylcarbazole; aminium salt;
D O I：
10.1016/S0040-4039(00)01046-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The efficient, regiospecific, and periselective Diels-Alder cycloadditions of N-(trans-1-propenyl)carbazole, a highly electron rich dienophile, to both acyclic and cyclic conjugated dienes is found to be induced by tris(4-bromophenyl)aminium hexachloroantimonate. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5997 / 6000
页数：4
相关论文
共 50 条
  • [1] Diels-Alder cycloadditions of the N-vinylcarbazole radical cation
    Bauld, NL
    Yang, JK
    Gao, DX
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (02): : 207 - 210
  • [2] ENANTIOSELECTIVE N-SULFINYL DIENOPHILE DIELS-ALDER CYCLOADDITIONS
    REMISZEWSKI, SW
    YANG, J
    WEINREB, SM
    TETRAHEDRON LETTERS, 1986, 27 (17) : 1853 - 1856
  • [3] Radical cation Diels-Alder cycloadditions by visible light photocatalysis
    Lin, Shishi
    Ischay, Michael A.
    Fry, Charles G.
    Yoon, Tehshik P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [4] Radical Cation Diels-Alder Cycloadditions by Visible Light Photocatalysis
    Lin, Shishi
    Ischay, Michael A.
    Fry, Charles G.
    Yoon, Tehshik P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) : 19350 - 19353
  • [5] Visible light photocatalysis of intramolecular radical cation Diels-Alder cycloadditions
    Lin, Shishi
    Padilla, Christian E.
    Ischay, Michael A.
    Yoon, Tehshik P.
    TETRAHEDRON LETTERS, 2012, 53 (24) : 3073 - 3076
  • [6] The cation radical chain cycloaddition polymerization of N,3-bis (trans-1-propenyl) carbazole:: The critical importance of intramolecular hole transfer in cation radical cycloaddition polymerization
    Roh, Y
    Gao, D
    Bauld, NL
    ADVANCED SYNTHESIS & CATALYSIS, 2001, 343 (05) : 481 - 489
  • [7] DIELS-ALDER REACTIONS USING N-(PARA-CHLOROSULFONYLPHENYL)-MALEIMIDE AS DIENOPHILE
    CREMLYN, R
    SWINBOURNE, F
    NUNES, R
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 33 (1-2): : 65 - 75
  • [8] Intramolecular site selectivity in cation radical Diels-Alder cycloadditions of difunctional and trifunctional dienophiles
    Bauld, NL
    Yang, JK
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2000, 13 (09) : 518 - 522
  • [9] An unprecedented cation radical chain Diels-Alder polymerization leading to novel carbazole polymers
    Bauld, NL
    Roh, Y
    TETRAHEDRON LETTERS, 2001, 42 (08) : 1437 - 1439
  • [10] APPLICATIONS OF N-SULFINYL DIENOPHILE DIELS-ALDER CYCLOADDITIONS TO SYNTHESIS OF UNUSUAL AMINO-SUGARS
    WEINREB, SM
    GAINOR, JA
    JOYCE, RP
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1986, 95 (11): : 1021 - 1031
12345