Disulfonimides

Benzenediazonium fluoroborate, 2-carboxy-xanthone synthesis from, 3, 838 Benzenediazonium ions phenyl azide formation from, 5, 839 Benzenediazonium salts, o-(imidazol-l-yl)-intramolecular diazo coupling, 5, 404 Benzene-1,2-disulfonimides N-substituted reactions, 6, 930 Benzene episulfide formation, 7, 577 Benzeneimine... 

The first examples were benzene disulfonimide derivatives prepared from o-benzenebis(sulfonyl chloride) or -disulfinic acid with amines or HNO2 respectively <84CHEC-I(6)914>, or benzothiazole derivatives (94) obtained from benzenesulfonamides or azides containing ortho SR or SOR groups... 

Figure 5.53 Schematic drawing of (a) [AuL2][N(S02-4-C6H4X)2], (b) bis(tetrahydrothtiophene)gold(l) benzene-1,2-disulfonimidate.

Reactions of hydrogenated derivatives including fluorination of disulfonimides and oxidation 1,3,2-dioxazolidines was an important subject considered in CHEC-II(1996) <1996CHEC-II(4)433>. 

N -Disulfonimides, RN(S02R )2, have been advanced as amine derivatives suitable for Sn2 processes, at least in those cases where R is a primary radical. N-(l-Decyl)-A(,lV-di(p-toluene)sulfonimide... 

NFoBS reacts with diethyl l-(ethoxycarbonyl)methylphosphonate in THF at -78°C in the presence of NaHMDS (1 eq) to afford the expected monofluorination product in 78% yield. The cyclic disulfonimide byproduct is highly water soluble and easy to remove by aqueous workup. 

Deamination of primary amines. The conversion of primary amines into N-sulfonamides under Schotten-Baumann conditions is the basis for the classical Hinsberg test. Baumgarten et aO have found that N-sulfonamides can be converted into N,N-disulfonimides, usually in high yield, by conversion into the sodium salt (NaH) and subsequent reaction with a sulfonyl chloride in DMF as solvent ... 

Hutchins et al. have since reported that the disulfonimides undergo nucleophilic displacement with borohydride anion in HMPT to give hydrocarbons. In the case of di-p-toluenesulfonimides temperatures of 150-175° and a twofold excess of borohydride are used in order to obtain reasonable reaction times. 

Disodium tetracarbonylfcrratc, 550-552 Disodium tetrachloropalladate, 45 Dispiro [ 2.0.2,4] deca-7,9-diene, 568 Disulfides, 231-232, 563, 586 N,N-Disulfonimides, 531 Dithallous ethylene glycolate, 186 Dithia[3.3J metacyclophanes, 85... 

Another promising reagent for the protection of alcohols and phenols as their p-methoxybenzyl ethers is N-(4-methoxybenzyl)-o-benzenedisulfonimide [1%.1, Scheme 4.196] - which reacts with the sodium alkoxide in THF at room temperature. The disulfonimide 196.1 (mp 146-147 C) is easily prepared from 4-methoxybenzylamine and o-benzenedisulfonyl chloride. 

Previously unknown (biaryl)hydroxyl acid catalysts, disulfonimides 196 were prepared in five steps from BINOL (14AGE8765). These Lewis acid precursors allowed for the catalysis of Mukaiyama aldol reactions at unprecedented rates. A microwave-assisted protocol was described for the preparation of cyclic sulfamides 197 these reactions do not use catalysts and show increased yields, shorter reaction times, and less polymeric by-product than traditional heating (14PS285). 

A BINOL-related disulfonimide catalyses vinylogous and bisvinylogous Mukaiyama aldols in high ee. Examples of a-, P-, and e-selective cases are described. ... 

Chiral disulfonimides of the general structure 236 have been used as highly efficient catalysts for reactions such as an asymmetric Mannich reaction of silyl ketene acetals with A/-Boc-amino sulfones (13JA15334) as well as an asymmetric three-component synthesis of homoaUylic amines (13AGE2573). Analogs of pyrrolo[l,2,5]benzothiadiazepine 237a and the... 

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