查看“︁噻丁环”︁的源代码

{{Chembox
| verifiedrevid = 415222710
| ImageFile = Thietan.png
|  ImageFile_Ref = {{Chemboximage|correct|??}}
|  ImageSize = 50
|  ImageName = Structural formula of thietane
| IUPACName = Thietane
| SytematicName = <!-- Thietane -->
| OtherNames =硫杂环丁烷
| Section1 = {{Chembox Identifiers
|  CASNo = 287-27-4
|   CASNo_Ref = {{cascite|correct|??}}
|  PubChem = 9251
|   PubChem_Ref = {{Pubchemcite|correct|PubChem}}
|  ChemSpiderID = 8895
|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|  EINECS = 206-015-0
|  UNNumber = 1993
|  Beilstein = 102383
|  SMILES = C1CSC1
|  StdInChI = 1S/C3H6S/c1-2-4-3-1/h1-3H2
|   StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|  StdInChIKey = XSROQCDVUIHRSI-UHFFFAOYSA-N
|   StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2 = {{Chembox Properties
|  C = 3
|  H = 6
|  S = 1
|  Appearance = 无色液体
|  Odor = 硫味
|  Density = 1.028 g cm<sup>-3</sup>
|  BoilingPtCL = 94
|  BoilingPtCH = 95}}
| Section3 = {{Chembox Hazards
|  EUClass = {{Hazchem F}}{{Hazchem Xn}}
|  RPhrases = {{R11}}, {{R22}}
|  SPhrases = {{S16}}
|  NFPA-H = 2
|  NFPA-F = 4
|  NFPA-R = 1
|  FlashPt = -11(9) °C
|  GHSSignalWord = DANGER
|  HPhrases = {{H-phrases|225|302}}
|  PPhrases = {{P-phrases|210}}
}}
}}
'''噻丁环'''（'''Thietane'''）是一种含硫的四元杂环化合物，化学式C<sub>3</sub>H<sub>6</sub>S。<ref>{{cite journal |last= Leśniak |first=S |coauthors=Lewkowski, J; Kudelska, W; Zając, A| title =Thietanes and Thietes: Monocyclic |journal =Comprehensive Heterocyclic Chemistry III |year=2008 |volume=2.07 |pages=389–428 |doi=10.1016/B978-008044992-0.00207-8|}}</ref><ref>{{cite journal |last=Block |first=E |coauthors=DeWang, M | title =Thietanes and Thietes: Monocyclic |journal =Comprehensive Heterocyclic Chemistry II |year=1996 |volume=1.24 |pages=773–802 |doi=10.1016/B978-008096518-5.00024-1|}}</ref>

==合成==
噻丁环可由碳酸丙二酯与硫氰化钾反应制得，该法产量不高：<ref>S. Searles, E. F. Lutz in: ''A new synthesis of small ring cyclic sulfides'' [[J. Am. Chem. Soc.]] 1958, 80, 3168. {{DOI|10.1021/ja01545a071}}</ref>

:<math>\mathrm{C_4H_6O_3 + \ KSCN \longrightarrow \ C_3H_6S + \ KOCN + \ CO_2}</math>

一个改进的方法是1,3-二溴丙烷与[[硫化钠]]的[[亲核取代反应]]：<ref>K. Nagasawa, A. Yoneta in: Chem. Pharm. Bull 1985, 33, 11, 5048–5052. {{ISSN|0009-2363}}, {{DOI|10.1248/cpb.33.5048}}</ref>

:<math>\mathrm{Br-(CH_2)_3-Br + \ Na_2S \longrightarrow \ C_3H_6S + 2 \ NaBr}</math>
==反应==
噻丁环能被亲核试剂进攻而开环，例如与正丁基锂生成不对称硫醚：<ref>F. G. Bordwell, H. M. Andersen, M. P. Burnett in:''The reaction of thiacyclopropanes and thiacyclobutanes with organolithium compounds'' [[J. Am. Chem. Soc.]] 1954, 76, 1082-1085. {{DOI|10.1021/ja01633a045}}</ref>。

:<math>\mathrm{C_3H_6S + \ C_4H_9Li \longrightarrow \ C_4H_9-S-C_3H_7}</math>

与卤素单质反应二聚成卤代过硫醚，例如噻丁环与溴的反应：<ref>J. M. Stewart, C. H. Burnside in:''Reactions of trimethylenesulfide with chlorine and bromine'' [[J. Am. Chem. Soc.]], 1953, 75, 243-244. {{DOI|10.1021/ja01097a517}}</ref>。

:[[File:Thietan_Disulfid.png|500px]]
==參考資料==
{{reflist}}
{{环状化合物}}
[[Category:含硫雜環]]