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Synthesis 1991; 1991(9): 785-786
DOI: 10.1055/s-1991-26574
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A Novel Formation of Thiocarbonyl Compounds from Phosphorus Ylides with Cyclic Polysulfide as the Sulfuration Reagent

Ryu Sato* , Shin-ichi Satoh
  • *Department of Resources Chemistry, Faculty of Engineering, Iwate University, Morioka 020, Japan
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Publication Date:
29 April 2002 (online)

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The reaction of cyclic polysulfides, such as 5H-1,2,3,4-benzotetrathiepin and 6H-1,2,3,4,5-benzopentathiocin as the sulfuration reagent with relatively stable phosphorus ylides affords efficiently thiocarbonyl compounds such as thioaldehydes and thioketones, which further react with 2,3-dimethyl-1,3-butadiene or cyclopentadiene in situ to give various 5,6-dihydro-2H-thiopyrans and 2-thiabicyclo[2.2.1]hept-5-enes in satisfactory yields.