A sulfinyl nitrene is a chemical compound with generic formula R-S(O)N, with oxygen and nitrogen both bonded to the sulfur atom.
Sulfinyl nitrenes can be generated from the unstable sulfinyl azides (R-SON<sub>3</sub>). However this reaction easily results in explosions and unpredictable results.
Sulfinyl nitrenes can be prepared from a sulfinylhydroxylamine, with RâÂÂOâÂÂN=S=O, by a reaction with an organometallic M-R<sub>1</sub> compound to yield R<sub>1</sub>SON.
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. The dominant state is the singlet state with charge separation and a double bond.
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-SO<sub>2</sub>NH<sub>2</sub>.
The reaction of a sulfinyl nitrene with sulfoxides results in a sulfonyl sulfoximde, with the oxygen joining the sulfinyl sulfur and its bond replaced by a double bond to nitrogen.
Trifluoromethyl sulfinyl nitrene (CF<sub>3</sub>S(O)N) has been produced as a gas, and isolated in a noble gas matrix.
Methoxysulfinyl nitrene (CH<sub>3</sub>OS(O)N) was also produced by decomposing the azide.
Sulfinyl nitrenes are distinct from sulfonyl nitrenes which have two oxygen atoms attached to the sulfur atom.
Thiazate or thionylimide ([NSO]<sup>âÂÂ</sup>) is an anion that exists as alkali metal salts. They can be formed by a tri-tert-butoxy metal reaction with a trimethylsilyl compound:
NaNSO, KNSO, RbNSO, CsNSO, (Me<sub>2</sub>N)<sub>3</sub>S<sup>+</sup>NSO<sup>âÂÂ</sup> and tris(dimethylamino)sulfonium [(Me<sub>2</sub>N)<sub>3</sub>S][NSO] salts are known.