Ring expansion and ring contraction observed in isopropenyldihydrofuran derivatives

被引:2
|
作者
Yamaguchi, S [1 ]
Sugioka, Y [1 ]
Kitagawa, Y [1 ]
Matsumoto, Y [1 ]
Yokoyama, H [1 ]
Hirai, Y [1 ]
机构
[1] Toyama Univ, Fac Sci, Dept Chem, Toyama 930, Japan
关键词
D O I
10.1246/bcsj.70.2777
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An intramolecular anhydride formation in 5-isopropenyl-4,5-dihydrofuran-2,3-dicarboxylic acid caused a new ring expansion to give 4,7-dihydro-6-methyloxepin-2,3-dicarboxylic anhydride (2b). An aminolysis of 2b with benzylamine gave a mixture of two isomeric carboxamides, N-benzyl-4,7-dihydro-6-methyloxepin-2-carboxamide and trans-1(benzyloxamoyl)-2-isopropenylcyclopropane. Also, the ring expansion and ring contraction are discussed.
引用
收藏
页码:2777 / 2780
页数:4
相关论文
共 50 条
  • [31] Pd-Catalyzed Ring-Contraction and Ring-Expansion Reactions of Cyclic Allyl Amines
    Zanda, Matteo
    SYNTHESIS-STUTTGART, 2011, (19): : A97 - A98
  • [32] Biosynthesis of Xenovulene A(R): formation of a cyclopentenone via a unique ring expansion-ring contraction mechanism
    Raggatt, ME
    Simpson, TJ
    ChicarelliRobinson, MI
    CHEMICAL COMMUNICATIONS, 1997, (22) : 2245 - 2246
  • [33] Palladium-Catalyzed Ring-Contraction and Ring-Expansion Reactions of Cyclic Allyl Amines
    Dubovyk, Igor
    Pichugin, Dmitry
    Yudin, Andrei K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (26) : 5924 - 5926
  • [34] Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework
    Zonker, Benjamin
    Becker, Jonathan
    Hrdina, Radim
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (18) : 4027 - 4031
  • [35] THERMAL AND PHOTOCHEMICAL RING EXPANSION OF SOME PHOSPHOLE DERIVATIVES
    HUGHES, AN
    SRIVANAV.C
    CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (06): : 874 - &
  • [36] The investigation of Ring Expansion in beta-lactam derivatives
    Ahn, C
    Oh, SJ
    Ha, JR
    Park, JH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3062 - U3063
  • [37] Ring expansion of a ring expanded carbene
    Garcia, Lucia
    Al Furaiji, Khalidah H. M.
    Wilson, David J. D.
    Dutton, Jason L.
    Hill, Michael S.
    Mahon, Mary F.
    DALTON TRANSACTIONS, 2017, 46 (36) : 12015 - 12018
  • [38] Double isomerization of oxetane amides to azetidine esters with ring expansion and contraction
    Kanoh, S
    Nishimura, T
    Kita, Y
    Ogawa, H
    Motoi, M
    Takani, M
    Tanaka, T
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07): : 2253 - 2256
  • [39] Easy ring expansion and contraction in Pt-Sn bonded metallacycles
    Janzen, MC
    Jenkins, HA
    Jennings, MC
    Rendina, LM
    Puddephatt, RJ
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (11): : 1713 - 1715
  • [40] A CYCLOHEXANE RING CONTRACTION
    ADDERLEY, CJ
    BADDELEY, GV
    HEWGILL, FR
    TETRAHEDRON, 1967, 23 (10) : 4143 - &