DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation

被引：259

作者：

Woolven, Holly ^{[1
]}

Gonzalez-Rodriguez, Carlos ^{[1
]}

Marco, Isabel ^{[1
]}

Thompson, Amber L. ^{[1
]}

Willis, Michael C. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 18期

基金：

英国工程与自然科学研究理事会;

关键词：

MEDIATED ONE-POT; TRIOXIDE COMPLEXES; ARYL HALIDES; ENE REACTION; DEOXYGENATION; ADDITIONS; NITRILES; SULFONES; SPECTRA;

D O I：

10.1021/ol201957n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and Iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.

引用

页码：4876 / 4878

页数：3

共 34 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2]

[Anonymous], 1995, ENCY REAGENTS ORGANI

[3]

[Anonymous], POLYMERIC MATERIALS

[4] CRYSTALS version 12: software for guided crystal structure analysis [J].

Betteridge, PW ;

Carruthers, JR ;

Cooper, RI ;

Prout, K ;

Watkin, DJ .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2003, 36 :1487-1487

[5] Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes [J].

Biswas, K ;

Prieto, O ;

Goldsmith, PJ ;

Woodward, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2232-2234

[6] Sulfur dioxide mediated one-pot, four-component synthesis of polyfunctional sulfones and sulfonamides, including medium-ring cyclic derivatives [J].

Bouchez, LC ;

Turks, M ;

Dubbaka, SR ;

Fonquerne, F ;

Craita, C ;

Laclef, S ;

Vogel, P .

TETRAHEDRON, 2005, 61 (48) :11473-11487

[7] Sulfur dioxide mediated one-pot, three- and four-component syntheses of polyfunctional sulfonamides and sulfonic esters: Study of the stereoselectivity of the ene reaction of sulfur dioxide [J].

Bouchez, LC ;

Dubbaka, SR ;

Turks, M ;

Vogel, P .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) :6413-6418

[8] CRYSTALS enhancements: dealing with hydrogen atoms in refinement [J].

Cooper, Richard I. ;

Thompson, Amber L. ;

Watkin, David J. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2010, 43 :1100-1107

[9] Ammonium amidosulphite [J].

Divers, E ;

Ogawa, M .

JOURNAL OF THE CHEMICAL SOCIETY, 1900, 77 :327-335

[10] TRIMETHYLAMINE-SO2, PROTOTYPE STRONG CHARGE-TRANSFER COMPLEX [J].

DOUGLAS, JE ;

KOLLMAN, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (16) :5226-5227

← 1 2 3 4 →