Dithiane: Difference between revisions
m Replace magic links with templates per local RfC and MediaWiki RfC |
added CSID and InChI(Key)s |
||
| Line 24: | Line 24: | ||
| SMILES2 = C1CSCCS1 |
| SMILES2 = C1CSCCS1 |
||
| SMILES2_Comment = (1,4-dithiane) |
| SMILES2_Comment = (1,4-dithiane) |
||
| ChemSpiderID = 120109 |
|||
| ChemSpiderID_Comment = (1,2-dithiane) |
|||
| StdInChI = 1S/C4H8S2/c1-2-4-6-5-3-1/h1-4H2 |
|||
| StdInChI_Comment = (1,2-dithiane) |
|||
| StdInChIKey = CXWGKAYMVASWDQ-UHFFFAOYSA-N |
|||
| StdInChIKey_Comment = (1,2-dithiane) |
|||
| ChemSpiderID1 = 10019 |
|||
| ChemSpiderID1_Comment = (1,3-dithiane) |
|||
| StdInChI1 = 1S/C4H8S2/c1-2-5-4-6-3-1/h1-4H2 |
|||
| StdInChI1_Comment = (1,3-dithiane) |
|||
| StdInChIKey1 = WQADWIOXOXRPLN-UHFFFAOYSA-N |
|||
| StdInChIKey1_Comment = (1,3-dithiane) |
|||
| ChemSpiderID2 = 10020 |
|||
| ChemSpiderID2_Comment = (1,4-dithiane) |
|||
| StdInChI2 = 1S/C4H8S2/c1-2-6-4-3-5-1/h1-4H2 |
|||
| CStdInChI2_Comment = (1,4-dithiane) |
|||
| StdInChIKey2 = LOZWAPSEEHRYPG-UHFFFAOYSA-N |
|||
| StdInChIKey2_Comment = (1,4-dithiane) |
|||
}} |
}} |
||
|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
||
Revision as of 14:13, 14 June 2017
 1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right)
| |
| Names | |
|---|---|
| Other names
Dithiacyclohexanes
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
| |
| |
| Properties | |
| C4H8S2 | |
| Molar mass | 120.23 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-CH
2- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane.
1,3-Dithianes
1,3-Dithianes are protecting group of some carbonyl-containing compounds due to their inertness to many conditions. They form by treatment of the carbonyl compound with 1,3-propanedithiol under conditions that remove water from the system.[1] The protecting group can be removed with mercuric reagents, a process that exploits the high affinity of Hg(II) for thiolates. 1,3-Dithianes are also employed in umpolung reactions, such as the Corey–Seebach reaction:[2]
Typically, in organic synthesis, ketones and aldehydes are protected as their dioxolanes instead of dithianes.
References
- ^ E. J. Corey, D. Seebach (1988). "1,3-Dithiane". Organic Syntheses; Collected Volumes, vol. 6, p. 556.
- ^ T. W. Green, P. G. M. Wuts, "Protective Groups in Organic Synthesis" Wiley-Interscience, New York, 1999. ISBN 978-0-471-69754-1.