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Sulfinyl nitrene

A sulfinyl nitrene is a chemical compound with generic formula R-S(O)N, with oxygen and nitrogen both bonded to the sulfur atom.

Preparation
Sulfinyl nitrenes can be generated from the unstable sulfinyl azides (R-SON3). However this reaction easily results in explosions and unpredictable results. Sulfinyl nitrenes can be prepared from a sulfinylhydroxylamine, with R–O–N=S=O, by a reaction with an organometallic M-R1 compound to yield R1SON. ==Properties==
Properties
Sulfinyl nitrenes are electrophilic. Sulfinyl nitrenes have a resonance structure between sulfur in a +6 oxidation state and a triple bond to nitrogen, or sulfur with a +4 state, nitrogen in +1 state and a single bond, or a positive charge on sulfur and a negative charge on nitrogen with a double bond. ==Reactions==
Reactions
Sulfinyl nitrenes are unstable and react with themselves to yield sulfonyl nitrenes, disulfides or polymerise to trioxotrithiztriazes. The reaction with water yields a sulfonylamide (R-SO2NH2. ==Examples==
Examples
Trifluoromethyl sulfinyl nitrene (CF3S(O)N) has been produced as a gas, and isolated in a noble gas matrix. ==Related==
Related
Sulfinyl nitrenes are distinct from sulfonyl nitrenes which have two oxygen atoms attached to the sulfur atom. or thionylimide ([NSO]−) is an anion that exists as alkali metal salts. They can be formed by a tri-tert-butoxy metal reaction with a trimethylsilyl compound: :KOtBu + Me3SiNSO → K[NSO] + Me3SiOtBu NaNSO, KNSO, RbNSO, CsNSO, (Me2N)3S+NSO− and tris(dimethylamino)sulfonium [(Me2N)3S][NSO] salts are known. ==References==
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