Formation of four-membered rings using the intramolecular Wittig reaction:: Convenient generation of functionalised butadienes

被引：0
|
作者：
Aitken, RA [1 ]
Balkovich, ME
Bestmann, HJ
Clem, O
Gibson, SE
Röder, T
机构：
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Erlangen Nurnberg, Inst Organ Chem, D-91054 Erlangen, Germany
来源：
SYNLETT | 1999年 / 08期
关键词：
phosphorus ylides; Wittig reactions; flash pyrolysis; gas-phase chemistry; cycloadditions;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Flash vacuum pyrolysis of the stable ylides 5, readily available by conjugate addition of ylides 3 to alpha,beta-unsaturated ketones 4, results in an intramolecular Wittig reaction with the delta-carbonyl to give cyclobutenes which under the conditions involved undergo electrocyclic ring-opening to afford the synthetically useful 1,3-dienes 7.
引用
收藏
页码：1235 / 1236
页数：2
相关论文
共 26 条
  • [1] Formation of Six-Membered Rings via Alkyne Insertion into Four-Membered Rings
    Matsuda, Takanori
    Miura, Norio
    Matsumoto, Takeshi
    INTERNATIONAL SYMPOSIUM ON APPLIED CHEMISTRY (ISAC) 2016, 2017, 1803
  • [2] The additive formation of four-membered rings Part III The nomenclature of four-membered heterocyclic rings, and the formation and properties of some derivatives of methylene-1 2 4-oxadi-imine
    Ingold, CK
    JOURNAL OF THE CHEMICAL SOCIETY, 1924, 125 : 87 - 102
  • [3] Quaternary ammonium salts from bromopropyldialkylammes IV Formation of four-membered rings
    Gibbs, CF
    Marvel, CS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 : 725 - 727
  • [4] INTRAMOLECULAR WITTIG REACTION OF ALPHA,ALPHA'-DIOXOCYCLOALKYLIDENETRIBUTYLPHOSPHORANES - FORMATION AND TRAPPING OF CYCLOALKYN-2-ONES WITH 5-MEMBERED AND 6-MEMBERED RINGS
    OHMORI, H
    MAEDA, H
    UEDA, C
    MASUI, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (13) : 874 - 875
  • [5] Synthesis of Polycyclic Arenes Composed of Four-, Five-, Six-, and Eight-Membered Rings via an Unexpected Four-Membered Ring Formation Reaction
    Hirota, Soshi
    Nakano, Sachiko
    Sugiyama, Haruki
    Segawa, Yasutomo
    ORGANIC LETTERS, 2023, 25 (45) : 8062 - 8066
  • [6] The additive formation of four-membered rings Part II The conditions which confer stability on the dimethinediazidines
    Ingold, CK
    Piggott, HA
    JOURNAL OF THE CHEMICAL SOCIETY, 1923, 123 : 2745 - 2752
  • [7] Studies on the Synthesis of Novel Four-Membered Cyclic Oxaphosphetanes via Intramolecular Mitsunobu Reaction of Bishydroxyalkylphosphinic Acids
    Kaboudin, Babak
    Haghighat, Hamideh
    Yokomatsu, Tsutomu
    SYNLETT, 2016, 27 (10) : 1537 - 1540
  • [8] Synthesis of cyclobutanones and four-membered enol ethers by using a rearrangement reaction of enol triflates
    Tanino, K
    Aoyagi, K
    Kirihara, Y
    Ito, Y
    Miyashita, M
    TETRAHEDRON LETTERS, 2005, 46 (07) : 1169 - 1172
  • [9] Coulomb repulsion versus cycloaddition: formation of anionic four-membered rings from sodium phosphaethynolate, Na(OCP)
    Heift, Dominikus
    Benko, Zoltan
    Gruetzmacher, Hansjoerg
    DALTON TRANSACTIONS, 2014, 43 (02) : 831 - 840
  • [10] Formation of BCBH/BCBCl Four-Membered Rings by Complexation of Boron- and Nitrogen-Substituted Acetylene with Hydro-/Chloroboranes
    Kobayashi, Akemi
    Suzuki, Katsunori
    Kitamura, Ryo
    Yamashita, Makoto
    ORGANOMETALLICS, 2020, 39 (03) : 383 - 387
123