77128-62-2

Upstream product

• 92497-27-3 (toluenesulfanyl)phenylacetylene 
• 108-98-5 thiophenol 
• 2408-88-0 2-benzylsulfanyl-1-phenylethanone 
• 77128-46-2 2-Benzylsulfanyl-1-phenyl-2-phenylsulfanyl-ethanone 
• 77128-47-3 (2-Oxo-2-phenyl-1-phenylsulfanyl-ethylsulfanyl)-acetic acid methyl ester 
• 67655-17-8 α-chloro-α-(phenylthio)acetophenone 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 77128-56-4 ((2R,3R)-3-Hydroxy-3-phenyl-2,3-dihydro-benzo[b]thiophen-2-ylsulfanyl)-acetic acid methyl ester 
• 77128-55-3 (2R,3R)-2-Benzylsulfanyl-3-phenyl-2,3-dihydro-benzo[b]thiophen-3-ol 

Relevant academic research and scientific papers

Thiol radical addition to alkynes. Sulfanyl radical addition and hydrogen atom abstraction relative reaction rates

2-(Toluenesulfanyl)- 1 and 2-(benzenesulfanyl)-phenylacetylene 10 reacted with benzenethiol and toluenethiol, respectively, in the presence of AIBN at 84 and 154°C to give products deriving from vinyl radicals 2 which undergo hydrogen abstraction reaction

PHOTOCHEMICAL RING CLOSURE OF α,α-BISULFENYLATED CARBONYL COMPOUNDS STEREOSELECTIVE FORMATION OF CIS-DIHYDROBENZOTHIOPHENES

Photochemistry of α,α-bisulfenylated ketone has been investigated.Irradiation of 2-phenylthiodihydrothiophen-3-one (1) in benzene gave the radical recombination products 9 (63percent) and 10 (49percent).In a polar solvent, the ionic chemistry became predominant.Brief irradiation of 1 in acetonitrile and methanol gave the cis-fused dihydrothiophene 11 as the major product in 43percent and 20percent yields, respectively.The stereoselective photocyclization was generally observed for other ketones (2-8) in acetonitrile solution (Table 1).The photoproducts were easily dehydrated by treating with boron trifluoride etherate to give the corresponding benzothiophenes in high yields.Simple α-phenylthioketones are photoinert under the same conditions.The mechanism of this novel photocyclization of bisulfenylated ketones is also discussed.

STEREOSPECIFIC PHOTOCYCLIZATION OF α-BISULFENYLATED KETO COMPOUNDS. CIS-DIHYDROBENZOTHIOPHENES.

Irradiation of α-bisulfenylated keto compounds in acetonitrile affords the cis-fused dihydrobenzothiophenes which are dehydrated to benzothiophenes in high yields.