2-Phenylthio-3,3,3-trifluoropropene, its sulfoxide and sulfone: Synthesis and reactivity in 1,3-dipolar cycloadditions.

被引:34
|
作者
Plancquaert, MA [1 ]
Redon, M [1 ]
Janousek, Z [1 ]
Viehe, HG [1 ]
机构
[1] UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
关键词
D O I
10.1016/0040-4020(96)00082-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Derivatives of 3,3,3-trifluoropropene 1 : alpha-sulfide 2, sulfoxide 3, sulfone 4 and bromide 6 are useful trifluoromethylated synthons. On reaction with diazo compounds, these derivatives can afford trifluoromethyl substituted pyrazolines, pyrazoles, cyclopropanes or allylsulfones in fair to excellent yields. 1,3-Dipolar cycloaddition of trifluoropropene derivatives 2-4 with N-benzylazomethine ylide provides disubstituted 3-trifluoromethyl-pyrrolidines.
引用
收藏
页码:4383 / 4396
页数:14
相关论文
共 50 条
  • [31] 1,3-DIPOLAR CYCLOADDITIONS OF AZIDOALKYL-PHOSPHONATES TO ENAMINES - SYNTHESIS OF DELTA(2)-1,2,3-TRIAZOLINES AND TRIAZOLES
    PALACIOS, F
    DERETANA, AMO
    PAGALDAY, J
    HETEROCYCLES, 1995, 40 (02) : 543 - 550
  • [32] Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to -oxo sulfines
    McCaw, Patrick G.
    Khandavilli, U. B. Rao
    Lawrence, Simon E.
    Maguire, Anita R.
    Collins, Stuart G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) : 622 - 638
  • [33] Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: efficient synthesis of functionalized 2-pyrazolines
    Lee, Sung Ii
    Kim, Ka Eun
    Hwang, Geum-Sook
    Ryu, Do Hyun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (09) : 2745 - 2749
  • [34] Unprecedented Synthesis of 3-Alkenyl-3-ethoxy-2-iminoketones via 1,3-Dipolar Cycloadditions of Nitrones with Alkynyl Fischer Carbene Complexes
    Ines Flores-Conde, Maria
    Angel Vazquez, Miguel
    Reyes, Leonor
    Tamariz, Joaquin
    Delgado, Francisco
    ORGANOMETALLICS, 2013, 32 (15) : 4244 - 4254
  • [35] AN EFFICIENT SYNTHESIS OF 2(5H)-FURANONE AND FURAN-DERIVATIVES USING 3-(PHENYLTHIO)PROPENAL AS A 1,3-DIPOLAR SYNTHON
    WATANABE, M
    TSUKAZAKI, M
    HIRAKAWA, Y
    IWAO, M
    FURUKAWA, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (11) : 2914 - 2919
  • [36] 1,3-DIPOLAR CYCLOADDITIONS OF ALKYL AZIDES WITH SULFONYL ISOTHIOCYANATES - SYNTHETIC METHOD FOR 1,2,3,4-THIATRIAZOLINES
    VANLOOCK, E
    VANDENSA.JM
    LABBE, G
    SMETS, G
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (16): : 2916 - 2917
  • [37] 1,3-DIPOLAR CYCLOADDITIONS OF AN AZIRIDINE VIA AZOMETHINE YLIDE TO 2-METHYLPYRIDAZIN-3(2H)-ONES
    FARINA, F
    MARTINRAMOS, MV
    ROMANACH, M
    HETEROCYCLES, 1995, 40 (01) : 379 - 386
  • [38] KINETICS OF 1,3-DIPOLAR CYCLOADDITIONS OF DIMETHYLACETYLENEDICARBOXYLATE TO COBALOXIME AZIDE, LCO(DH)2N3, COMPLEXES
    HSIEH, BT
    TAKACH, NE
    MILOSAVLJEVIC, EB
    NELSON, JH
    KEMMERICH, T
    BECK, W
    BRESCIANIPAHOR, N
    RANDACCIO, L
    BROWER, KR
    INORGANICA CHIMICA ACTA, 1987, 134 (01) : 31 - 42
  • [39] Tosylhydrazide-Promoted Diastereoselective Intramolecular 1,3-Dipolar Cycloadditions: Synthesis of Tetrahydropyrrolo[3,4-c]pyrazoles
    Barroso, Raquel
    Escribano, Maria
    Cabal, Maria-Paz
    Valdes, Carlos
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (08) : 1672 - 1683
  • [40] A stereoselective method for the synthesis of enantiopure 3-substituted 4-hydroxyproline derivatives via 1,3-dipolar cycloadditions
    Brahmi, Jihed
    Aouadi, Kaiss
    Msaddek, Moncef
    Praly, Jean-Pierre
    Vidal, Sebastien
    COMPTES RENDUS CHIMIE, 2016, 19 (08) : 933 - 935