3354-40-3Relevant academic research and scientific papers
Sulfur-Containing Heterocycles Derived by Reaction of ω-Keto Amides with Lawesson's Reagent
Nishio, Takehiko
, p. 1207 - 1214 (2007/10/03)
The reaction of ω-keto amides with Lawesson's reagent (LR: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) is described. Treatment of 3-keto amides (2-acylacetamides) 1 with LR gave the corresponding 3-keto thioamides 2, along with 1,2-dithiole-3-thiones 3. Treatment of 4-keto amides, 3-acyl propionamides 5, with LR yielded five-membered heterocycles, pyrroles 6 and/or 2-aminothiophenes 7. 5-Keto amides, 3-benzoyl butyramides 8, reacted with LR to give dihydrothiopyran-2-thione 9 as the sole product, but in low yield. 2-Acylbenzamides 10 also reacted with LR to afford 3-mercaptoisoindolin-2-ones 11 or dihydroisobenzothiophene-1-thiones 12.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XL. THERMAL HETEROCYCLIZATION OF BIS(3-CHLORO-2-BUTENYL) DISULFIDE
Turchaninova, L. P.,Sukhomazova, E. N.,Levanova, E. P.,Korchevin, N. A.,Deryagina, E. N.,Voronkov, M. G.
, p. 1995 - 1998 (2007/10/02)
The thermolysis of bis(3-chloro-2-butenyl) disulfide in a stream of nitrogen (350-500 deg C) leads to 3-thiophenethiol and 5-methyl-1,2-dithiole-3-thione with an overall yield of up to 45percent.The radical path for the formation of these products and, particularly, the participation of sulfhydryl radicals (HS) in the process is discussed.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXXIV. THERMOLYSIS OF DIBUTYL POLYSULFIDES
Sukhomazova, E. N.,Turchaninova, L. P.,Korchevin, N. A.,Deryagina, E. N.,Voronkov, M. G.
, p. 1059 - 1062 (2007/10/02)
The main liquid product from the thermolysis of dibutyl polysulfides (C4H9)2Sn at 500-550 deg C is thiophene (maximum yield 43 percent with n = 3).The most thermally labile is dibutyl tetrasulfide, which decomposes even at 250 deg C.Above 350 deg C the tetrasulfide is also converted into 5-methyl-1,2-dithiole-3-thione, the yield of which amounts to 5-6percent.During the thermolysis of dibutyl disulfide in the presence of acetylene even at 400 deg C thiophene is formed with a yield of 70percent but in a mixture with benzene (yield 25 percent).
