Ring-Opening 1,3-Dichlorination of Donor-Acceptor Cyclopropanes by Iodobenzene Dichloride

被引：103
|
作者：
Garve, Lennart K. B. [1 ]
Barkawitz, Philip [1 ]
Jones, Peter G. [1 ]
Werz, Daniel B. [1 ]
机构：
[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 21期
关键词：
SUBSTITUTED CYCLOPROPANES; 3+2 CYCLOADDITION; 1,2-CYCLOPROPANATED SUGARS; ASYMMETRIC-SYNTHESIS; AMINOCYCLOPROPANES; ALDEHYDES; ANNULATION; FURAN; TETRAHYDROFURANS; REARRANGEMENTS;
D O I：
10.1021/ol5029139
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Donor-acceptor cyclopropanes are reacted with iodobenzene dichloride to afford ring-opened products bearing chlorine atoms in the 1- and 3-positions, adjacent to the donor and acceptor groups. A variety of different donors (e.g., alkyl, aryl, N, and O) and acceptor moieties (e.g., ketones, diesters, and dinitriles) are used.
引用
收藏
页码：5804 / 5807
页数：4
相关论文
共 50 条
  • [11] DONOR-ACCEPTOR SUBSTITUTED CYCLOPROPANES - SYNTHESIS AND RING-OPENING TO 1,4-DICARBONYL COMPOUNDS
    REISSIG, HU
    HIRSCH, E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (10): : 813 - 814
  • [12] Ring-Opening Reactions of Donor-Acceptor Cyclopropanes with Enolizable 5-Mercapto-1H-tetrazoles
    Mloston, Grzegorz
    Celeda, Malgorzata
    Kowalczyk, Mateusz
    Oliver, Gwyndaf A.
    Werz, Daniel B.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [13] Asymmetric ring-opening of donor-acceptor cyclopropanes with primary arylamines catalyzed by a chiral heterobimetallic catalyst
    Luo, Weiwei
    Wang, Hong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [14] Asymmetric Ring-Opening of Donor-Acceptor Cyclopropanes with Primary Arylamines Catalyzed by a Chiral Heterobimetallic Catalyst
    Luo, Weiwei
    Sun, Zhicheng
    Fernando, E. H. Nisala
    Nesterov, Vladimir N.
    Cundari, Thomas R.
    Wang, Hong
    ACS CATALYSIS, 2019, 9 (09) : 8285 - 8293
  • [15] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
    Cavitt, Marchello A.
    Phun, Lien H.
    France, Stefan
    CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
  • [16] Ring Opening of Donor-Acceptor Cyclopropanes with N-Nucle-ophiles
    Budynina, Ekaterina M.
    Ivanov, Konstantin L.
    Sorokin, Ivan D.
    Melnikov, Mikhail Ya.
    SYNTHESIS-STUTTGART, 2017, 49 (14): : 3035 - 3068
  • [17] Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
    Boichenko, Maksim A.
    Andreev, Ivan A.
    Chagarovskiy, Alexey O.
    Levina, Irma I.
    Zhokhov, Sergey S.
    Trushkov, Igor V.
    Ivanova, Olga A.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 1146 - 1157
  • [18] Nucleophilic ring opening of imidazolone activated donor-acceptor cyclopropanes with alcohols
    Ikonnikova, Viktoria A.
    Zhigileva, Ekaterina A.
    Kuleshov, Andrei, V
    Shirokova, Vasilissa V.
    Baranov, Mikhail S.
    Mikhaylov, Andrey A.
    MENDELEEV COMMUNICATIONS, 2021, 31 (05) : 657 - 658
  • [19] Triazene-Activated Donor-Acceptor Cyclopropanes: Ring-Opening and (3+2) Annulation Reactions
    Suleymanov, Abdusalom A.
    Le Du, Eliott
    Dong, Zhaowen
    Muriel, Bastian
    Scopelliti, Rosario
    Fadaei-Tirani, Farzaneh
    Waser, Jerome
    Severin, Kay
    ORGANIC LETTERS, 2020, 22 (11) : 4517 - 4522
  • [20] Benzotriazole-Triggered Three-Component Lewis Acid-Catalyzed Ring-Opening 1,3-Aminofunctionalization of Donor-Acceptor Cyclopropanes
    Deswal, Shiksha
    Guin, Avishek
    Biju, Akkattu T.
    ORGANIC LETTERS, 2023, 25 (10) : 1643 - 1648
12345