PHTHALIMIDESULFENYL CHLORIDE .4. ADDITION TO ACETYLENES AND SYNTHETIC UTILIZATION OF THEIR ADDUCTS

被引:27
作者
CAPOZZI, G
GORI, L
MENICHETTI, S
NATIVI, C
机构
[1] Centro C.N.R. 'Chimica e Struttura dei Composti Eterociclici e loro Applicazioni', Dipartimento di Chimica Organica, Universita' di Firenze, I-50121, Firenze
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 15期
关键词
D O I
10.1039/p19920001923
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both the stereo- and regio-chemical reactivity of the phthalimidesulfenyl chloride 1 towards symmetrical and terminal acetylenes and the reactivity of the adducts 3 and 5 with various nucleophiles has been investigated. Nucleophilic substitution of the phthalimide residue was achieved with MeLi, PhLi, Bu(t)Li, (Me3Si)2NNa and Me3SiSMe. The synthesis of beta-chlorovinyl tributylstannyl sulfides 14. is also described. The synthetic potential of the new sulfur compounds is discussed.
引用
收藏
页码:1923 / 1928
页数:6
相关论文
共 30 条
  • [1] SOME REACTIONS OF SILYL-SULPHUR AND GERMYL-SULPHUR COMPOUNDS WITH SII-N BOND
    ARMITAGE, DA
    CLARK, MJ
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1970, 24 (03) : 629 - &
  • [2] BARTON DHR, 1970, J CHEM SOC CHEM COMM, P1466
  • [3] PREPARATION OF EPISULFIDES FROM ALKENES VIA SUCCINIMIDE-N-SULFENYL CHLORIDE OR PHTHALIMIDE-N-SULFENYL CHLORIDE ADDUCTS
    BOMBALA, MU
    LEY, SV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12): : 3013 - 3016
  • [4] BOUSTANY SK, 1970, TETRAHEDRON LETT, V11, P3547
  • [5] GENERATION OF THIONITROSOARENES (ARN=S) FROM N-(ARYLAMINOTHIO)PHTHALIMIDES AND INSITU TRAPPING WITH ALKENES AND CONJUGATED DIENES
    BRYCE, MR
    TAYLOR, PC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (12): : 3225 - 3235
  • [6] BUSI E, 1992, IN PRESS SYNTHESIS
  • [7] H-1 AND C-13 NUCLEAR MAGNETIC-RESONANCE EVIDENCE FOR A LONG-LIVED THIIRENIUM ION
    CAPOZZI, G
    DELUCCHI, O
    LUCCHINI, V
    MODENA, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (07) : 248 - 249
  • [8] PHTHALIMIDOSULPHENYL CHLORIDE - A SYNTHETIC EQUIVALENT OF INACCESSIBLE SULFENYL CHLORIDES
    CAPOZZI, G
    GORI, L
    MENICHETTI, S
    [J]. TETRAHEDRON LETTERS, 1990, 31 (43) : 6213 - 6216
  • [9] DIMERIC CATIONS FROM ALKANESULFENYL CHLORIDES - ELUSIVE NATURE OF SULPHENYLIUM IONS
    CAPOZZI, G
    LUCCHINI, V
    MODENA, G
    RIVETTI, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (04): : 361 - 366
  • [10] REACTIONS OF SULFENYL CHLORIDES AND DISULFIDES IN ACIDIC MEDIA - TRAPPING OF ALKYL(BISALKYLTHIO)SULPHONIUM ION INTERMEDIATES
    CAPOZZI, G
    LUCCHINI, V
    MODENA, G
    RIVETTI, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (09): : 900 - 903