BETA-(N,N-DIALKYLAMINO)ETHYL ARYLTHIOSULFONATES - NEW SIMULANTS FOR O-ETHYL S-[2-(DIISOPROPYLAMINO)ETHYL] METHYLPHOSPHONOTHIOATE

被引：11

作者：

DAVIS, FA ^{[1
]}

RAY, JK ^{[1
]}

KASPEROWICZ, S ^{[1
]}

PRZESLAWSKI, RM ^{[1
]}

DURST, HD ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 09期

关键词：

D O I：

10.1021/jo00035a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beta-(N,N-Dialkylamino)ethyl arylthiosulfonates 2, new simulants for the hydrolysis and oxidation chemistry of VX (1), are prepared in good yield by reaction of a potassium arylthiosulfonate with a 2-chloroethylamine. Alkaline hydrolysis of 2 results in cleavage of the S-S bond to give sulfinic acids and disulfides. Like VX, oxidation of 2 by N-sulfonyloxaziridine 12 occurs exclusively on nitrogen to give the corresponding amine oxide which subsequently undergoes a Cope elimination reaction affording the vinyl sulfide 14.

引用

页码：2594 / 2599

页数：6

共 22 条

[1]

BODOR N, 1988, APR P US ARM CHEM RE, P81

[2] CHEMISTRY OF SULFENIC ACIDS .7. REASON FOR THE HIGH REACTIVITY OF SULFENIC ACIDS - STABILIZATION BY INTRAMOLECULAR HYDROGEN-BONDING AND ELECTRONEGATIVITY EFFECTS [J].

DAVIS, FA ;

JENKINS, LA ;

BILLMERS, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1033-1040

[3] CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE [J].

DAVIS, FA ;

SHEPPARD, AC ;

CHEN, BC ;

HAQUE, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6679-6690

[4] APPLICATIONS OF OXAZIRIDINES IN ORGANIC-SYNTHESIS [J].

DAVIS, FA ;

SHEPPARD, AC .

TETRAHEDRON, 1989, 45 (18) :5703-5742

[5] REACTION OF THIOLSULFONATE GROUP WITH AROMATIC NUCLEUS - A NEW RING CLOSURE [J].

DUNBAR, JE ;

TARNOWSK.BH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1967, 4 (03) :339-&

[6] THE CHLORINE-CATALYZED HYDROLYSIS OF ISOPROPYL METHYLPHOSPHONOFLUORIDATE (SARIN) IN AQUEOUS SOLUTION [J].

EPSTEIN, J ;

BAUER, VE ;

SAXE, M ;

DEMEK, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) :4068-4071

[7] MICELLAR ACCELERATION OF ORGANOPHOSPHATE HYDROLYSIS BY HYDROXIMINOMETHYLPYRIDINIUM TYPE SURFACTANTS [J].

EPSTEIN, J ;

KAMINSKI, JJ ;

BODOR, N ;

ENEVER, R ;

SOWA, J ;

HIGUCHI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2816-2821

[8]

Epstein J., 1974, PHOSPHORUS, V4, P157

[9]

GIVSON DT, 1937, J CHEM SOC, P487

[10]

HALEY MV, 1919, ASTM STP, V1096, P60

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