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噻丁环（Thietane）是一种含硫的四元杂环化合物，化学式C₃H₆S。^[1]^[2]

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：^[3]

\mathrm {C_{4}H_{6}O_{3}+\ KSCN\longrightarrow \ C_{3}H_{6}S+\ KOCN+\ CO_{2}}

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：^[4]

\mathrm {Br-(CH_{2})_{3}-Br+\ Na_{2}S\longrightarrow \ C_{3}H_{6}S+2\ NaBr}

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：^[5]。

\mathrm {C_{3}H_{6}S+\ C_{4}H_{9}Li\longrightarrow \ C_{4}H_{9}-S-C_{3}H_{7}}

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：^[6]。

^ Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A. Thietanes and Thietes: Monocyclic. Comprehensive Heterocyclic Chemistry III. 2008, 2.07: 389–428. doi:10.1016/B978-008044992-0.00207-8.
^ Block, E; DeWang, M. Thietanes and Thietes: Monocyclic. Comprehensive Heterocyclic Chemistry II. 1996, 1.24: 773–802. doi:10.1016/B978-008096518-5.00024-1.
^ 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
^ K. Nagasawa, A. Yoneta in: Chem. Pharm. Bull 1985, 33, 11, 5048–5052. ISSN 0009-2363, doi:10.1248/cpb.33.5048
^ 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
^ 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