Iodination of tricyclo[4.1.0.02,7]heptane in the presence of external nucleophiles

被引:5
|
作者
Vasin, VA [1 ]
Semenov, AV
Razin, VV
机构
[1] Mordovian NP Ogarev State Univ, Saransk 430000, Russia
[2] St Petersburg State Univ, St Petersburg, Russia
关键词
D O I
10.1023/A:1020382903063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tricyclo[4.1.0.0(2.7)]heptane reacted with iodine, N-iodosuccinimide, and iodine monochloride in the presence of external nucleophiles yielding products of conjugate endo,syn addition at the central C-1-C-7 bond. The mechanism of these chemo- and stereoselective reactions is discussed.
引用
收藏
页码:803 / 809
页数:7
相关论文
共 50 条
  • [21] Nitrochlorination of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone
    V. A. Vasin
    S. G. Kostryukov
    A. V. Semenov
    V. V. Razin
    Russian Journal of Organic Chemistry, 2008, 44 : 528 - 531
  • [22] Synthesis of Tricyclo[4.4.0.02,7]decane Derivatives from Tricyclo[4.1.0.02,7]heptane Precursors
    V. A. Vasin
    D. Yu. Korovin
    V. V. Razin
    P. S. Petrov
    Russian Journal of Organic Chemistry, 2019, 55 : 415 - 425
  • [23] Synthesis of Tricyclo[4.4.0.02,7]decane Derivatives from Tricyclo[4.1.0.02,7]heptane Precursors
    Vasin, V. A.
    Korovin, D. Yu.
    Razin, V. V.
    Petrov, P. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (04) : 415 - 425
  • [24] ENTHALPY OF METAL-CATALYZED ISOMERIZATIONS OF QUADRICYCLANE AND OF TRICYCLO[4.1.0.02,7]HEPTANE
    WIBERG, KB
    CONNON, HA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (17) : 5411 - 5412
  • [25] STEREOSELECTIVITY OF THE PHENYLTHIYL RADICAL ATTACK ON THE CENTRAL BOND OF TRICYCLO[4.1.0.02,7]HEPTANE
    DIETZ, P
    SZEIMIES, G
    CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (01): : 398 - 400
  • [26] Radical Reactions of Tricyclo[4.1.0.02,7]heptane Derivatives with Arenesulfonylethynyl(trimethyl)silanes
    Kostryukov, S. G.
    Masterova, Yu. Yu.
    Korovin, D. Yu.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (04) : 582 - 587
  • [27] Radical Reactions of Tricyclo[4.1.0.02,7]heptane Derivatives with Arenesulfonylethynyl(trimethyl)silanes
    S. G. Kostryukov
    Yu. Yu. Masterova
    D. Yu. Korovin
    Russian Journal of Organic Chemistry, 2020, 56 : 582 - 587
  • [28] SUBSTITUTION EFFECT ON PHOTOISOMERIZATION OF 1-PHENYL-TRICYCLO[4.1.0.02,7]HEPTANE
    FUJITA, K
    NAKAMURA, T
    MATSUI, K
    SHONO, T
    TETRAHEDRON LETTERS, 1975, (49) : 4385 - 4388
  • [29] THE INFLUENCE OF METHYL SUBSTITUTION ON THE PHOTOSENSITIZED REACTIONS OF TRICYCLO-[4.1.0.02,7]HEPTANE
    GASSMAN, PG
    OLSON, KD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1982, 184 (SEP): : 46 - ORGN
  • [30] Reaction products of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and tricyclo[4.1.0.02,7]hept-1-yl phenyl sulfone with dinitrogen tetraoxide
    Vasin, V. A.
    Kostryukov, S. G.
    Bolusheva, I. Yu.
    Razin, V. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (04) : 511 - 515