Author:
Ding Mingyan,Willis Michael
Abstract
image
[7522‐26‐1]
C
3
H
9
NOSSi
(MW 135.3)
InChI =
1S/C3H9NOSSi/c1‐7(2,3)4‐6‐5/h1‐3H3
InChIKey =
RFMSRGPUQNDFNS‐UHFFFAOYSA‐N
(used as a sulfurdiimidation, sulfinamidation, or sulfinylamination reagent for the synthesis of aza‐sulfur compounds, as a dienophile in Diels–Alder reactions, and as a dipolarophile in (3 + 2) cycloadditions)
Alternative Names
: 1,1,1‐trimethyl‐
N
‐sulfinylsilanamine, silylamine, 1,1,1‐trimethyl‐
N
‐sulfinyl‐, (sulfinylamino)trimethylsilane, (trimethylsilyl)sulfinylamine, (trimethylsilyl)sulfinylimide, 1,1,1‐trimethyl‐
N
‐sulfinylsilylamine,
N
‐(trimethylsilyl)sulfinylimide,
N
‐trimethylsilylsulfinylimine,
N
‐sulfinyl trimethylsilanamine, ((trimethylsilyl)imino)‐λ
4
‐sulfanone, and TMS‐NSO.
Physical Data
: mp −78 °C,
1
bp 108–110 °C (760 mmHg),
1
and = 1.4258.
2
Solubility
: miscible with common organic solvents including THF, Et
2
O, CH
2
Cl
2
, CHCl
3
, toluene, and benzene.
Form Supplied in
: colorless liquid; commercially available.
Analysis of Reagent Purity
: spectroscopic data: IR,
1,3
Raman,
3
NMR (
1
H,
13
C,
14
N,
17
O,
29
Si),
3
and mass spectra.
1,3
Preparative Method
: TMS‐NSO is prepared from the reaction of (SiMe
3
)
3
N and SOCl
2
in anhydrous CH
2
Cl
2
at room temperature for 20 h,
4
or from PhSNSO by heating with Me
3
SiSPh at 100 °C for 1 h.
2
Distillation then affords TMS‐NSO.
Purification
: distillation.
Handling, Storage, and Precautions
: TMS‐NSO is sensitive to moisture and air, and its use after storage is challenging.