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

页码：1923 / 1928

页数：6

共 30 条

[1] SOME REACTIONS OF SILYL-SULPHUR AND GERMYL-SULPHUR COMPOUNDS WITH SII-N BOND [J].

ARMITAGE, DA ;

CLARK, MJ .

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 [J].

BOMBALA, MU ;

LEY, SV .

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 [J].

BRYCE, MR ;

TAYLOR, PC .

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 [J].

CAPOZZI, G ;

DELUCCHI, O ;

LUCCHINI, V ;

MODENA, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (07) :248-249

[8] PHTHALIMIDOSULPHENYL CHLORIDE - A SYNTHETIC EQUIVALENT OF INACCESSIBLE SULFENYL CHLORIDES [J].

CAPOZZI, G ;

GORI, L ;

MENICHETTI, S .

TETRAHEDRON LETTERS, 1990, 31 (43) :6213-6216

[9] DIMERIC CATIONS FROM ALKANESULFENYL CHLORIDES - ELUSIVE NATURE OF SULPHENYLIUM IONS [J].

CAPOZZI, G ;

LUCCHINI, V ;

MODENA, G ;

RIVETTI, F .

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 [J].

CAPOZZI, G ;

LUCCHINI, V ;

MODENA, G ;

RIVETTI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (09) :900-903

← 1 2 3 →