Sulfimidation of thio-ether crown systems: the X-ray crystal structure of the {[9-ane]S2S(NH2)}+, {[9-ane]SS(NH2)S(NH2)}2+, and {[9-ane]S(NH2)S2( -N)}2+ cations
Treatment of the thio-ether crown [9-ane]S 3 ( 1 ) with 1 equiv of O-mesitylsulfonylhydroxylamine (MSH) yields the water-soluble protonated sulfimide {[9-ane]S 2 S(NH 2 )} + ( 2 ). Two equiv of MSH leads to the formation of {[9-ane]SS(NH 2 )S(NH 2 )} 2+ ( 3 ), while excess MSH generates the {[9-ane]...
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| Published in | Canadian journal of chemistry Vol. 80; no. 11; pp. 1410 - 1414 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Ottawa, Canada
NRC Research Press
01.11.2002
|
| Online Access | Get full text |
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| Summary: | Treatment of the thio-ether crown [9-ane]S
3
(
1
) with 1 equiv of O-mesitylsulfonylhydroxylamine (MSH) yields the water-soluble protonated sulfimide {[9-ane]S
2
S(NH
2
)}
+
(
2
). Two equiv of MSH leads to the formation of {[9-ane]SS(NH
2
)S(NH
2
)}
2+
(
3
), while excess MSH generates the {[9-ane]S(NH
2
)S
2
( -N)}
2+
cation (
4
) (
24
form as salts of the [Me
3
C
6
H
2
SO
3
]
anion); the X-ray crystal structure of
2
and
3
confirms that one and two of the ring sulfurs, respectively, have been converted to terminal protonated sulfimides, while that of
4
reveals the presence of both terminal and bridging nitrogens.Key words: sulfur-nitrides, macrocycles, sulfimides, amination. |
|---|---|
| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v02-051 |