A facile two-carbon ring expansion process based on the 2-cyano-1-vinylcycloalkanolsystem

被引:9
|
作者
Shia, KS [1 ]
Jan, NW
Zhu, JL
Ly, TW
Liu, HJ
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
[2] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
ring transformations; alcohols; cyano compounds; ketones;
D O I
10.1016/S0040-4039(99)01401-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Upon exposure to potassium hydride in THF in the presence of 18-crown-6, several 2-cyano-1-vinylcycloalkanol derivatives were found to undergo ring enlargement to give the corresponding gamma-cyano cycloalkanones in synthetically useful yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6753 / 6756
页数:4
相关论文
共 50 条
  • [1] A novel and highly efficient two-carbon ring expansion
    Ruedi, G
    Nagel, M
    Hansen, HJ
    ORGANIC LETTERS, 2003, 5 (22) : 4211 - 4213
  • [2] Ring expansion and contraction of a two-carbon bridged spiropentane
    Wiberg, KB
    Snoonian, JR
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05): : 1390 - 1401
  • [3] Allyl sulfoxides as precursors for radical two-carbon ring expansion of cyclobutanones
    Chuard, R
    Giraud, A
    Renaud, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (22) : 4323 - 4325
  • [4] Synthesis of macrocyclic ketones by repeatable two-carbon ring expansion reactions
    Nagel, M
    Fráter, G
    Hansen, HJ
    CHIMIA, 2003, 57 (04) : 196 - 199
  • [5] Two-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon-Carbon Bonds
    Xia, Ying
    Ochi, Shusuke
    Dong, Guangbin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (33) : 13038 - 13042
  • [6] Two-carbon ring expansion of β-lactams via N(1)-C(4) cleavage reactions
    Cabell, LA
    McMurray, JS
    TETRAHEDRON LETTERS, 2002, 43 (14) : 2491 - 2493
  • [7] Two-carbon ring expansion of isatin: a convenient construction of a dibenzo[b,d] azepinone scaffold
    Shi, Rong-Guo
    Wang, Xiao-Hua
    Liu, Ruzhang
    Yan, Chao-Guo
    CHEMICAL COMMUNICATIONS, 2016, 52 (37) : 6280 - 6283
  • [8] Cascade rearrangement of spiroepoxymethyl radicals into 2-oxocycloalkyl radicals: evaluation of a two-carbon cycloalkanone ring expansion
    Afzal, M
    Walton, JC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (05): : 937 - 945
  • [9] Two-carbon ring expansion of cyclobutanone skeletons by nickel-catalyzed intermolecular alkyne insertion
    Murakami, Masahiro
    Ashida, Shinji
    Matsuda, Takanori
    TETRAHEDRON, 2006, 62 (32) : 7540 - 7546
  • [10] Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two-Carbon Ring-Expansion
    Tymann, Dina Christina
    Benedix, Lars
    Iovkova, Lyuba
    Pallach, Roman
    Henke, Sebastian
    Tymann, David
    Hiersemann, Martin
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (52) : 11974 - 11978