3334-00-7Relevant academic research and scientific papers
Reactions of the Chlorine Complex of Tetrahydrothiophene
Schmidt, Donald L.,Heeschen, Jerry P.,Klingler, Thomas C.,McCarty, Leslie P.
, p. 2840 - 2847 (2007/10/02)
The chlorine complex of tetrahydrothiophene (THT) undergoes the Pummerer reaction to yield not only the expected 2-chloro- and 2,3-dichlorotetrahydrothiophene products but also 1-(2-chlorotetrahydro-3-thienyl)-tetrahydrothiophenium chloride (10), which upon hydrolysis yields 1-(tetrahydro-2-hydroxy-3-thienyl)tetrahydrothiophenium chloride 3 and upon elimination of HCl produces 1-(4,5-dihydro-3-thienyl)tetrahydrothiophenium chloride (2).The sulfonium 10 was formed by the addition of the chlorine-THT complex to the Pummerer-derived 2,3-dihydrothiophene.The sulfonium formation was monitored in CCl4, CH2Cl2, and liquid SO2 by proton NMR, and the addition of the complex to cyclohexene, dihydrofuran, styrene, and thiophene was studied.There was a dramatic increase in reactivity of the complex in sulfur dioxide both to addition and substitution type reactions.
