Carbonyl groups at positions C2 and C3 enhance stereochemical inversion at C7 in norbornane compounds

被引：4
|
作者：
Jenkins, MN [1 ]
Nash, JJ [1 ]
Morrison, H [1 ]
机构：
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 20期
关键词：
S(N)2 displacement; norbornanes; electric field effect;
D O I：
10.1016/S0040-4039(02)00611-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
It is known that the presence of a carbonyl group at C2 in norbornane compounds aids in the S(N)2 displacement of substituents at C7. In this study, we report a significant enhancement in reactivity at C7 by a second carbonyl group at C3. These diketones undergo rapid inversion at 80degreesC, while the monoketone does not exhibit any reactivity at this temperature. The increase in reactivity is attributed to electric field effects. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3773 / 3775
页数：3
相关论文
共 50 条
  • [1] C1, C2, C3, C4, C5, C6, C7, C8 (anti-CEA)
    Kim, SH
    HYBRIDOMA AND HYBRIDOMICS, 2001, 20 (5-6): : 408 - 408
  • [2] TRANSITIVE SUBMANIFOLDS OF C2 AND C3
    SVEC, A
    CZECHOSLOVAK MATHEMATICAL JOURNAL, 1973, 23 (02) : 306 - 338
  • [3] ADDITIONAL FORMS OF C2 AND C3
    KOETHE, S
    GIGLI, I
    AUSTEN, KF
    FEDERATION PROCEEDINGS, 1971, 30 (02) : A472 - &
  • [4] Absolute electron impact ionization cross-sections and polarizability volumes for the C2 to C6 methanoates and C3 to C7 ethanoates
    Hudson, JE
    Weng, ZF
    Vallance, C
    Harland, PW
    INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2006, 248 (1-2) : 42 - 46
  • [5] A concise synthesis of C2′-C7′ fragment of aigialomycin D
    Zhang Hong-Kui
    Chen Wei-Qiang
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2007, 28 (04): : 689 - 691
  • [6] Pyrazolopyridine antiherpetics:: SAR of C2′ and C7 amine substituents
    Johns, BA
    Gudmundsson, KS
    Turner, EM
    Allen, SH
    Samano, VA
    Ray, JA
    Freeman, GA
    Boyd, FL
    Sexton, CJ
    Selleseth, DW
    Creech, KL
    Moniri, KR
    BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (07) : 2397 - 2411
  • [7] CHROMATOGRAPHIC SEPARATION OF C3 CARBONYL COMPOUNDS
    ANDREEV, LV
    INDUSTRIAL LABORATORY, 1966, 32 (09): : 1303 - &
  • [8] Palladium-Catalyzed Regioselective C-H Arylation of 4-Azaindazole at C3, C5 and C7 Positions
    Faarasse, Soukaina
    El Kazzouli, Said
    Bourzikat, Otmane
    Bourg, Stephane
    Aci-Seche, Samia
    Bonnet, Pascal
    Suzenet, Franck
    Guillaumet, Gerald
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (16) : 3937 - 3945
  • [9] Studies on the Total Synthesis of Hainanolide（Ⅳ）-Revising the Stereochemistry of C2α-H and Introducing the Two Hydroxy Groups at C3β,C4α Positions
    Wen Qian YANG
    Xiao Ming YU
    Shi Zhi CHEN
    Liang HUANG(Institute of Materia Medica
    ChineseChemicalLetters, 1997, (12) : 0 - 0
  • [10] C2 AND C3 PAIN DERMATOMES IN MAN
    POLETTI, CE
    CEPHALALGIA, 1991, 11 (03) : 155 - 159
12345