Sulfinyl nitrene
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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-SON3). However this reaction easily results in explosions and unpredictable results.[1][2]
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.[1]
Properties
Sulfinyl nitrenes are electrophilic.[1]
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.[1] The dominant state is the singlet state with charge separation and a double bond.[3]
Reactions
Sulfinyl nitrenes are unstable and react with themselves to yield sulfonyl nitrenes, disulfides or polymerise to trioxotrithiztriazes.[4]
The reaction with water yields a sulfonylamide (R-SO2NH2.[4]
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.[5]