80716-54-7Relevant academic research and scientific papers
Cationic Polar Cycloadditions of Phenylthionium Ions with Olefines: A New Route to Thiochromans
Ishibashi, Hiroyuki,Okada, Motofumi,Sato, Kazumi,Ikeda, Masazumi,Ishiyama, Ko-ichi,Tamura, Yasumitsu
, p. 90 - 95 (2007/10/02)
Reaction of 2-chloro-N,N-dimethyl-2-(phenylthio)acetamide (1a) with styrene in the presence of stannic chloride gave 3,4-dihydro-N,N-dimethyl-4-phenyl-2H-1-benzothiopyran-2-carboxamide.The same benzothiopyran was also obtained from N,N-dimethyl-2-(phenylsulfinyl)acetamide and styrene under the Pummerer reaction conditions, but in lower yield.Similarly, α-chlorosulfides derived from ethyl 2-(phenylthio)acetate, 2-(phenylthio)acetonitrile, 1-(phenylthio)-2-propanone, and thioanisole reacted with styrene to give the corresponding 4-phenylbenzothiopyrans in variable yields.The reaction of 1a with trans-stilbene gave the expected benzothiopyran derivative, but the reaction of 1a with 1,1-diphenylethylene and phenylacetylene showed some variation of the reaction course.This cycloaddition reaction was extended to the intramolecular case.A possible mechanism for the formation of the benzothiopyran is discussed.
CATIONIC POLAR CYCLOADDITION WITH CHLOROMETHYL PHENYL SULFIDES
Tamura, Y.,Ishiyama, K.,Mizuki, Y.,Maeda, H.,Ishibashi, H.
, p. 3773 - 3774 (2007/10/02)
Chloromethyl phenyl sulfides 3 underwent ++2>type polar cycloadditions with styrene, trans-stilbene, and phenylacetylene in the presence of stannic chloride to afford the thiochroman 4, 5 and thiochromen derivatives 6.Under the same reaction
