Synthesis of Sulfondiimines by N-Chlorosuccinimide-Mediated Oxidative Imination of Sulfiliminium Salts

被引：35

作者：

Candy, Mathieu ^{[1
]}

Guyon, Carole ^{[1
]}

Mersmann, Stefanie ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 18期

关键词：

imination; N-chlorosuccinimide; sulfiliminium salts; sulfondiimines; synthetic methods; DIARYL SULFONE DIIMIDES; S; S-DIALKYLSULFUR DIIMIDES; CONVENIENT PREPARATION; SULFOXIMINES; INHIBITORS; ANALOGS; ARYL; FLUORO-LAMBDA(6)-SULFANENITRILES;

D O I：

10.1002/anie.201201296

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Access to sulfondiimines: The oxidative one-pot chlorination-imination sequence of in situ generated free sulfilimines by N-chlorosuccinimide (NCS) allows the preparation of N-monosubstituted sulfondiimines under mild reaction conditions with excellent functional-group tolerance (see scheme; Mes=2,4,6-trimethylphenylsulfonyl) Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4440 / 4443

页数：4

共 43 条

[1] ZUR KENNTNIS NICHTMETALLISCHER IMINVERBINDUNGEN .18. UBER DIE CHLORAMINIERUNG VON THIOATHERN [J].

APPEL, R ;

FEHLHABE.HW ;

HANSSGEN, D ;

SCHOLLHO.R .

CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (10) :3108-&

[2] NONMETALLIC IMINE COMPOUNDS .37. N-THIOCYANATO AND N-CYANO DERIVATIVES OF S,S-DIMETHYLSULFODIIMINE [J].

APPEL, R ;

VOLLMER, G .

CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (08) :2555-&

[3] NON-METALLIC COMPOUNDS .41. SYNTHESIS OF N-ALKYL-S,S-DIMETHYLSULFODIIMIDES [J].

APPEL, R ;

KOHNKE, J .

CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (06) :2023-&

[4] Biological characterization of sulfoxaflor, a novel insecticide [J].

Babcock, Jonathan M. ;

Gerwick, Clifford B. ;

Huang, Jim X. ;

Loso, Michael R. ;

Nakamura, Genta ;

Nolting, Steven P. ;

Rogers, Richard B. ;

Sparks, Thomas C. ;

Thomas, James ;

Watson, Gerald B. ;

Zhu, Yuanming .

PEST MANAGEMENT SCIENCE, 2011, 67 (03) :328-334

[5] CHROMATOGRAPHIC RESOLUTION OF CHIRAL DRUGS ON POLYAMIDES AND CELLULOSE TRIACETATE [J].

BLASCHKE, G .

JOURNAL OF LIQUID CHROMATOGRAPHY, 1986, 9 (2-3) :341-368

[6]

Christensen B. W., 1975, J CHEM SOC CHEM COMM, P784

[7] REACTION OF CHLORAMINE WITH ALKYL SULFIDES [J].

COGLIANO, JA ;

BRAUDE, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (06) :1397-&

[8] Highly symmetrical amino acid-derived N,N′-diacylated sulfodiimines [J].

Dehli, JR ;

Bolm, C .

SYNTHESIS-STUTTGART, 2005, (07) :1058-1060

[9] Synthesis and structure of novel 1λ4,2,6-thiadiazines [J].

Diederich, WE ;

Haake, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3817-3830

[10] A new method for the preparation of fluoro-λ6-sulfanenitriles:: reaction of sulfimides with Selectfluor™ [J].

Fujii, T ;

Asai, S ;

Okada, T ;

Hao, W ;

Morita, H ;

Yoshimura, T .

TETRAHEDRON LETTERS, 2003, 44 (33) :6203-6205

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