151608-64-9

Upstream product

• 4091-26-3 β-styrenesulfonyl chloride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 

Downstream Products

• 147355-32-6 C₁₃H₁₈F₃NO₂SSi 
• 151608-65-0 C₁₁H₁₆ClNOSSi 

Relevant academic research and scientific papers

Sulfonimidates and method for preparing same

This invention provides novel organosulfonimidates and a method for preparing both the present sulfonimidates and those disclosed in the prior art. Some of the sufonimidates can be condensed under relatively mild conditions to form polyorganooxothiazenes.

Novel synthesis of sulfonimidoyl halides and sulfonimidates from N-Silylated sulfonamides and dihalophosphoranes

In the past, general methods for the preparation of sulfonimidoyl chlorides have involved oxidation of sulfur-(IV) compounds with various oxidizing agents. For the purpose of studying the thermal decomposition of suitably substituted sulfonimidates to sulfur-nitrogen based polymeric materials, a simple method was developed for the synthesis of sulfonimidoyl halides from readily available sulfur(VI) starting materials. Unsubstituted sulfonamides are known to react with Ph3P-CCl4 to produce only N-phosphoranylidenesulfonamides. In contrast, we have found that the reaction of N-silylated sulfonamides [RSO2NHSiMe3 (6), RSO2N(SiMe3)2 (7)] with Ph3PCl2 in CHCl3 yields N-trimethylsilylsulfonimidoyl chlorides, Me3SiN=S(O)(R)Cl, 11, except when the group R is strongly electronegative, like CF3. Further, the reaction of 7 (R = Me) with Ph3PBr2 in CH2Cl2 produced the first detectible sulfonimidoyl bromide, Me3SiN=S(O)(Me)Br, 12. The sulfonimidoyl chlorides 11 were converted (in one-pot reactions) to 2,2,2-trifluoroethyl-, phenyl-, or ethyl N-trimethylsilylsulfonimidates 3 (R = Me, Et, ClCH32CH2CH2, PhCH=CH, Ph, 4-F-C6H4). In preliminary reactions, it was found that the N-silylsulfonimidates can in turn be derivatized by taking advantage of the susceptibility of the Si-N bond to cleavage.

Method for preparing sulfonimidoyl halides

N-triorganosilylsulfonimidoyl halides are prepared using a novel series of reactions from compounds of hexavalent sulfur selected from amides, chlorides and anhydrides of organosulfonic acids. More specifically, the present method relates to the reaction of an N-triorganosilyl- or an N,N-bis(triorganosilyl)-sulfonamide with a triorganodihalophosphorane to form the corresponding sulfonimidoyl halide.