UNUSUAL REACTION OF GRIGNARD-REAGENTS WITH BIS(TRIFLUOROMETHYL)DISULFIDE

被引：16

作者：

MUNAVALLI, S ^{[1
]}

ROSSMAN, DI ^{[1
]}

ROHRBAUGH, DK ^{[1
]}

FERGUSON, CP ^{[1
]}

机构：

[1] USA,EDGEWOOD RES DEV & ENGN CTR,ABERDEEN PROVING GROUND,MD 21010

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1993年 / 61卷 / 1-2期

关键词：

D O I：

10.1016/S0022-1139(00)80425-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Simultaneous scission of the C-S and S-S bonds of bis(trifluoromethyl)disulfide occurs on treatment with Grignard reagents at -78-degrees-C and gives rise to unsymmetrical disulfides and sulfides as well as alkyl sulfides. Under similar experimental conditions, alkyl disulfides are recovered unreacted. Probable mechanisms of the cleavage reactions are presented.

引用

页码：147 / 153

页数：7

共 33 条

[1] MASS-SPECTRAL STUDIES OF UNSYMMETRICAL DIALKYL DISULFIDES - INTRA-MOLECULAR 1,2-HYDROGEN 1,3-HYDROGEN AND 1,4-HYDROGEN MIGRATION PROCESSES [J].

ALONSO, ME ;

ARAGONA, H ;

CHITTY, AW ;

COMPAGNONE, R ;

MARTIN, G .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (23) :4491-4495

[2] CONCERNING THE MECHANISM OF GRIGNARD-REAGENT FORMATION - EVIDENCE FOR RADICAL ESCAPE AND RETURN TO THE SURFACE OF MAGNESIUM [J].

ASHBY, EC ;

OSWALD, J .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6068-6076

[3] A DETAILED DESCRIPTION OF THE MECHANISM OF REACTION OF GRIGNARD-REAGENTS WITH KETONES [J].

ASHBY, EC .

PURE AND APPLIED CHEMISTRY, 1980, 52 (03) :545-569

[4] THIOPHILIC ADDITION OF PHENYLLITHIUM TO THIOBENZOPHENONE [J].

BEAK, P ;

WORLEY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (13) :4142-&

[5] REACTION OF GRIGNARD REAGENT FROM NEOPENTYL CHLORIDE WITH BENZOPHENONE . A NUCLEAR MAGNETIC RESONANCE STUDY [J].

BLOMBERG, C ;

SALINGER, RM ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08) :2385-&

[6] FORMATION OF GRIGNARD COMPOUNDS .5. REACTION OF IODOMETHANE WITH MAGNESIUM IN ALLYL PHENYL ETHER - 2ND-ORDER CIDNP SPECTRUM [J].

BODEWITZ, HWJJ ;

SCHAART, BJ ;

VANDERNIET, JD ;

BLOMBERG, C ;

BICKELHAUPT, F ;

HOLLANDER, JAD .

TETRAHEDRON, 1978, 34 (16) :2523-2527

[7] CONTROLLED CARBON-SULFUR OR CARBON-SILICON BOND-CLEAVAGE IN THE REACTIONS OF ALKYL-LITHIUM REAGENTS WITH A 1-SILYL-1-THIOALLENE [J].

BRIDGES, AJ ;

FEDIJ, V ;

TUROWSKI, EC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (19) :1093-1095

[8] FACILE PHOTOCHEMICAL OR OXYGEN INITIATED FREE-RADICAL CHAIN REACTIONS OF TRIALKYLBORANES WITH ORGANIC DISULFIDES - CONVENIENT NEW SYNTHESIS OF ORGANIC SULFIDES VIA HYDROBORATION [J].

BROWN, HC ;

MIDLAND, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (13) :3291-&

[9]

BURTON H, 1968, J CHEM SOC, P525

[10]

BURTON H, 1968, J CHEM SOC, P528

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