Thiete is a
heterocyclic compound containing an
unsaturated four-membered ring with three carbon atoms and one sulfur atom.[1][2][3] It is more commonly encountered not on its own, but in
anellated derivatives, several of which have been synthesized. Thietes are generally not very stable.[4]
Structure
Thiete is a
valence isomer of the compound thio
acrolein (CH2=CHCH=S) and undergoes ring opening to it at temperatures below 400°C.[5] Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.[6]
Derivatives
Benzothietes are thietes annulated to benzo group. Such species are prepared by
flash vacuum pyrolysis of 2-mercapto
benzyl alcohols. They are precursors to other S-heterocycles.[7]
Thiete 1,1-dioxides are
sulfones, the parent being C3H4SO2. They are more stable than the parent thietes.[8] Substituted thiete-1,1-dioxides can also be prepared by [2+2]
cycloaddition of
sulfenes and ynamines.
^Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III. 2 (7): 389–428.
doi:
10.1016/B978-008044992-0.00207-8.
^Block, E (2007). "Thietes and Derivatives". Sci. Synth. 33: 187–202.
^Block, E; DeWang, M (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II. 1 (24): 773–802.
doi:
10.1016/B978-008096518-5.00024-1.
^Dittmer, DC; Davis, FA (1965). "Evidence for a Thiete (Thiacyclobutene)". J. Am. Chem. Soc. 87 (9): 2064–2065.
doi:
10.1021/ja01087a048.
^Block, Eric; Wang, Ming De (1996). "Thietanes and Thietes: Monocyclic". In Katritzky, Alan R.; Rees, Charles W.; Scriven, Eric F. V. (eds.). Comprehensive Heterocyclic Chemistry II. Vol. 1B (2nd ed.). Elsevier. p. 780.
ISBN978-0-08-096518-5.
^Herbert Meier , Axel Mayer, Dieter Gröschl "Benzothietes—versatile Synthons For The Preparation Of Heterocycles" Sulfur Reports, 1994, volume 16, 23-56,
doi:
10.1080/01961779408048965
^Thomas C. Sedergran and Donald C. Dittmer "Thiete 1,1-dioxide and Chlorothiete 1,1-dioxide" Org. Synth. 1984, vol. 62, 210.
doi:
10.15227/orgsyn.062.0210