Diels-Alder reactivity of a ketovinylphosphonate with cyclopentadiene and furan.

被引：27
|
作者：
McClure, CK [1 ]
Hansen, KB [1 ]
机构：
[1] UNIV DELAWARE, DEPT CHEM & BIOCHEM, NEWARK, DE 19716 USA
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期
关键词：
D O I：
10.1016/0040-4039(96)00235-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Diels-Alder reactions between diethyl ketovinylphosphonate 5 and cyclopentadiene or furan were performed with and without Lewis acid assistance. The acetyl group directed endo in all cases, with ratios varying from 1.4:1 - 6.7:1 (acetyl endo).
引用
收藏
页码：2149 / 2152
页数：4
相关论文
共 50 条
  • [1] COPOLYMERIZATION OF MALEIC-ANHYDRIDE WITH CYCLOPENTADIENE AND FURAN AND ROLE OF DIELS-ALDER ADDUCTS
    GAYLORD, NG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1976, 172 (SEP3): : 77 - 77
  • [2] Ab initio and semiempirical modelling of stereoselectivities of Diels-Alder cycloaddition of furan and cyclopentadiene with norbornenes
    Margetic, D
    Warrener, RN
    CROATICA CHEMICA ACTA, 2003, 76 (04) : 357 - 363
  • [3] Interplay of structure and reactivity in a most unusual furan Diels-Alder reaction
    Griffith, Gerry A.
    Hillier, Ian H.
    Moralee, Andrew C.
    Percy, Jonathan M.
    Roig, Ricard
    Vincent, Mark A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) : 13130 - 13141
  • [4] REARRANGEMENT OF DIELS-ALDER ADDUCT OF AZODIBENZOYL AND CYCLOPENTADIENE
    MACKAY, D
    CAMPBELL, JA
    JENNISON, CP
    CANADIAN JOURNAL OF CHEMISTRY, 1970, 48 (01): : 81 - &
  • [5] DIELS-ALDER REACTIVITY OF VINYLSULFOXYALLENES
    WANG, XH
    DONOVALOVA, J
    HOLLIS, A
    JOHNSON, D
    RODRIGUEZ, A
    KENNEDY, GD
    KRISHNAN, G
    BANKS, H
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (04) : 871 - 876
  • [6] The origin of the halogen effect on reactivity and reversibility of Diels-Alder cycloadditions involving furan
    Pieniazek, SN
    Houk, KN
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) : 1442 - 1445
  • [7] DIFFERENTIAL THERMAL ANALYSIS OF DIELS-ALDER REACTION OF CYCLOPENTADIENE
    BARRETT, EJ
    HOYER, HW
    SANTORO, AV
    TETRAHEDRON LETTERS, 1968, (05) : 603 - &
  • [8] Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones
    Brimble, MA
    McEwan, JF
    Turner, P
    TETRAHEDRON-ASYMMETRY, 1998, 9 (07) : 1239 - 1255
  • [9] Diels-Alder cycloaddition of cyclopentadiene to a bis-naphthoquinone
    Brimble, MA
    Duncalf, LJ
    MOLECULES, 2000, 5 (02) : 162 - 166
  • [10] CHIRAL BUTENOLIDES IN DIELS-ALDER CYCLOADDITIONS WITH ISOPRENE AND CYCLOPENTADIENE
    ORTUNO, RM
    BATLLORI, R
    BALLESTEROS, M
    MONSALVATJE, M
    CORBERA, J
    SANCHEZFERRANDO, F
    FONT, J
    TETRAHEDRON LETTERS, 1987, 28 (29) : 3405 - 3408
12345