999-99-5Relevant academic research and scientific papers
Synthesis, characterization, and theoretical analysis of soluble poly(oxothiazenes): The ambient temperature lewis acid catalyzed in situ polymerization of N-silylsulfonimidoyl chlorides
Aldeva, Victoria,Gezahegn, Sossina,Panahi, Babak,Shuoprasad, Michelle,Ward, Jon,Foucher, Daniel A.,Gossage, Robert A.,McWilliams, Andrew R.
, p. 2562 - 2568 (2013/05/22)
The ambient temperature condensation, to yield low molecular weight poly(methyloxothiazene) (Mw = 1 × 104; PDI = 1.4), can be achieved by the reaction of MeS(O2)NHSiMe3 and SOCl2 - this latter reactio
Novel synthesis of sulfonimidoyl halides and sulfonimidates from N-Silylated sulfonamides and dihalophosphoranes
Roy, Aroop K.
, p. 2598 - 2601 (2007/10/02)
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
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, (2008/06/13)
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.
