Competitive 5-exo vs 6-exo ring closure in intramolecular electrophile-induced etherification reactions

被引:0
|
作者
Ramana, CV
Murali, R
Ravikumar, K
Nagarajan, M
机构
[1] UNIV HYDERABAD,SCH CHEM,HYDERABAD 500046,ANDHRA PRADESH,INDIA
[2] INDIAN INST CHEM TECHNOL,CRYSTALLOG LAB,HYDERABAD 500007,ANDHRA PRADESH,INDIA
来源
关键词
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-(Prop-2-enyl)hex-5-en-1-ol (1) and erythro-1,4-bis(cyclohex-2-enyl)butane-2,3-diol (9) undergo competitive intramolecular cyclization to give exclusively tetrahydrofuran derivatives without giving any tetrahydropyran derivatives.
引用
收藏
页码:226 / 227
页数:3
相关论文
共 48 条
  • [31] Intramolecular carbolithiation cascades as a route to a highly strained carbocyclic framework: competition between 5-exo-trig ring closure and proton transfer
    Bailey, William F.
    Fair, Justin D.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 537 - 543
  • [32] RING-CLOSURE TO YNONE SYSTEMS - 5-ENDO-DIG AND 6-ENDO-DIG AND 6-EXO-DIG MODES
    BRENNAN, CM
    JOHNSON, CD
    MCDONNELL, PD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (08): : 957 - 961
  • [33] DISTINGUISHING THE INVOLVEMENT OF ENDO VS EXO HYDROGEN IN REACTIONS OF FEC5H6+ IN THE GAS-PHASE
    BAKHTIAR, R
    JACOBSON, DB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 385 - INOR
  • [34] Fe(III)/Cu(II) mediated 5- and 6-exo oxidative ring expansion/cyclisation of cyclopropyl ethers:: studies towards dictyol C and α-eudesmol
    Booker-Milburn, KI
    Cox, B
    Grady, M
    Halley, F
    Marrison, S
    TETRAHEDRON LETTERS, 2000, 41 (23) : 4651 - 4655
  • [35] Visible light-induced N-radical 5-exo/6-endo cyclization of alkenyl amides: facile access to isoindolinones/isoquinolinones
    Lei, Zhen-Yao
    Hu, Kui
    He, Yuan-Xiang
    Geng, Shu
    Chen, Li-Na
    Zou, Shuai
    Pan, Li
    Ding, Zhi-Jun
    Huang, Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (12) : 2397 - 2401
  • [36] ACTIVATION OF 6-ENDO OVER 5-EXO EPOXIDE OPENINGS - RING-SELECTIVE FORMATION OF TETRAHYDROPYRAN SYSTEMS AND STEREOCONTROLLED SYNTHESIS OF THE ABC RING FRAMEWORK OF BREVETOXIN-B
    NICOLAOU, KC
    DUGGAN, ME
    HWANG, CK
    SOMERS, PK
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (19) : 1359 - 1362
  • [37] 6-ENDO-DIG VS 5-EXO-DIG RING-CLOSURE IN ORTHO-HYDROXYARYL PHENYLETHYNYL KETONES - A NEW APPROACH TO THE SYNTHESIS OF FLAVONES AND AURONES
    GARCIA, H
    IBORRA, S
    PRIMO, J
    MIRANDA, MA
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (23): : 4432 - 4436
  • [38] Nickel-catalyzed reductive arylalkylation of alkenes: 5-exo cyclization vs. 6-endo cyclization vs. 1,2-aryl migration to 6-endo product
    Du, Yuxin
    Wu, Hongli
    Yang, Miao
    She, Yuanbin
    Yang, Yun-Fang
    DALTON TRANSACTIONS, 2025,
  • [39] REACTION OF ALPHA-DIKETONES WITH 2-AMINO ALCOHOLS - INTRAMOLECULAR COMPETITIVE 6-EXO-TRIG VS 5-ENDO-TRIG PROCESSES - A SYSTEMATIC AND KINETIC-STUDY
    ALCAIDE, B
    PLUMET, J
    RODRIGUEZCAMPOS, IM
    GARCIABLANCO, S
    MARTINEZCARRERA, S
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08): : 2446 - 2454
  • [40] COMPETITIVE INTRAMOLECULAR AMINOLYSIS - RELATIVE RATES OF 5-MEMBERED AND 6-MEMBERED LACTAM RING-CLOSURE
    PATTERSON, KH
    DEPREE, GJ
    ZENDER, JA
    MORRIS, PJ
    TETRAHEDRON LETTERS, 1994, 35 (02) : 281 - 284