Sulfur diimide

Names
IUPAC name

diimino-λ4-sulfane

Other names

2λ4-Diazathia-1,2-diene

Identifiers

3D model (JSmol)

* Interactive image

ChemSpider |

* 298618

PubChem CID

* 336934

InChI

* InChI=1S/H2N2S/c1-3-2/h1-2H

Key: HQFYRKYAKZRZCJ-UHFFFAOYSA-N

SMILES

* N=S=N

Properties

Chemical formula

| H2N2S
Molar mass | 62.09 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Sulfur diimides are chemical compounds of the formula S(NR)2. Structurally, they are the diimine of sulfur dioxide. The parent member, S(NH)2, is of only theoretical interest. Other derivatives where R is an organic group are stable and useful reagents.

## Contents

* 1 Organic derivatives
* 2 Structure, bonding, reactions
* 3 See also
* 4 References

## Organic derivatives

Structure of S(NBu-t)2.

A particularly stable derivative is di-t-butyl‍sulfurdiimide.[1] It is prepared by reaction of tert-butylamine with sulfur dichloride to give the intermediate "S(N-t-Bu)", which decomposes at 60 °C to give the diimide. A second route to sulfur diimides involve treatment of sulfur tetrafluoride with amines. A third route involves transimidation of disulfonylsulfodiimide:

S(NSO2Ph)2 \+ 2 RNH2 → S(NR)2 \+ 2 PhSO2NH2

N,N'-Bis(methoxycarbonyl)sulfur diimide (MeO2C-N=S=N-CO2Me) is obtained from methyl carbamate.[2]

## Structure, bonding, reactions

These compounds are related to SO2. They have planar C–N=S=N–C cores with bent C–N=S and N=S=N geometries, and various combinations of E and Z isomers are observed for the two N=S bonds.[3]

Sulfur diimides are electrophilic. They undergo Diels–Alder reactions with dienes.[1] Organolithium reagents attack at the sulfur to give the corresponding nitrogen anion:

R'Li + S(NR)2 → R'S(NR)(NRLi)

The triimido analogues of sulfite can be generated by treating the sulfur diimides with a metal amide:[4]

4 LiNHBu-t + 2 S(NBu-t)2 → 2 Li2S(NBu-t)3 \+ 2 t-BuNH2

## See also

* Carbodiimide \- the carbon analogue
* Disulfur dinitride
* Bis(trimethylsilyl)sulfur diimide

## References

1. ↑ 1.0 1.1 Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167. doi:10.1002/anie.196701491
2. ↑ Kresze, Günter; Braxmeier, Hans; Münsterer, Heribert (1987). "Allylcarbamates by the Aza-Ene Reaction: Methyl N-(2-Methyl-2-Butenyl)Carbamate". Organic Syntheses 65: 159. doi:10.15227/orgsyn.065.0159.
3. ↑ Lork, Enno; Mews, Ruëdiger; Shakirov, Makhmut M.; Watson, Paul G.; Zibarev, Andrey V. (2002). "The first N-alkyl-N′-polyfluorohetaryl sulfur diimide". Journal of Fluorine Chemistry 115 (2): 165–168. doi:10.1016/S0022-1139(02)00047-7.
4. ↑ Fleischer, R.; Stalke, D., "A new route to sulfur polyimido anions S(NR)nm-: reactivity and coordination behavior", Coord. Chem. Rev. 1998, 176, 431-450. doi:10.1016/S0010-8545(98)00130-1

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*[CID]: Compound ID