Sulfinyl nitrene
# 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 $(R-SON_3).$ 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 $M-R_1$ compound to yield $R_1SON.$

## 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. The dominant state is the singlet state with charge separation and a double bond.

## 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 $(R-SO_2NH_2.$

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.

## Examples

Trifluoromethyl sulfinyl nitrene $(CF_3S(O)N)$ has been produced as a gas, and isolated in a noble gas matrix.

Methoxysulfinyl nitrene $(CH_3OS(O)N)$ was also produced by decomposing the azide.

## Related

Sulfinyl nitrenes are distinct from sulfonyl nitrenes which have two oxygen atoms attached to the sulfur atom.

Thiazate 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:

$KO^tBu$ + $Me_3SiNSO$ → K[NSO] + $Me_3SiO^tBu$

NaNSO, KNSO, RbNSO, CsNSO, $(Me_2N)_3S^+NSO^−$ and tris(dimethylamino)sulfonium $[(Me_2N)_3S][NSO]$ salts are known.

