80345-24-0Relevant academic research and scientific papers
Sulfenyl chloride chemistry. New precursors for diatomic sulfur transfer
Abu-Yousef, Imad A.,Harpp, David N.
, p. 8654 - 8660 (2007/10/03)
When triphenylmethanesulfenyl chloride (1) (or its thio homologue 2) are treated with various bicycles, norbornene (5), or bicyclo[2.2.2]octene (6), dithio adducts 7 and 8 were produced in good isolated yields. Final products were obtained via an episulfide intermediate. The stereochemistry of addition has been determined by X-ray analysis. Treatment of thiosulfenyl chloride 2 (or its dithio homologue 3) with other olefins, cyclopentene (10), cyclohexene (11), or 1,4-dioxene (12), leads to the formation of disulfides (13-15 from 2) and trisulfides (16 and 17 from 3) in high isolated yields (ca. 92%). The structures of 7, 8, and 13-17 were established by 1H and 13C NMR and elemental analysis as well as by X-ray determination. When these adducts are warmed with a 1,3-diene 42, they deliver diatomic sulfur- trapped derivatives, cyclic di-49 and tetrasulfide adducts 46. A variety of solvents, temperatures, times, and concentrations were employed to optimize the yield of 46 and 49. The tetrasulfide adduct 46 is quantitatively converted to disulfide 49 with triphenylphosphine; this affords cyclic disulfides in > 50% isolated yield from the diene. In addition, evidence has been obtained implicating dithietane intermediate 4.
Sulfenyl chloride chemistry, sulfur transfer to double bonds
Abu-Yousef,Hynes,Harpp
, p. 4289 - 4292 (2007/10/02)
When triphenylmethanesulfenyl chloride (1) (or its thio homolog 2) are treated with various bicycles, 1,2 addition reactions take place. Final products occur via an episulfide intermediate. The stereochemistry of addition has been determined by x-ray analysis. Finally, evidence has been obtained for the delivery of diatomic sulfur, likely via intermediate 3.
AN UNUSUAL REACTION OF TRIPHENYLMETHYLSULFENYL CHLORIDE WITH NORBORNENE AND NORBORNADIENE
Majewski, Jacek M.,Zakrzewski, Janusz
, p. 3659 - 3662 (2007/10/02)
Triphenylmethylsulfenyl chloride reacts with norbornene and norbornadiene to yield chlorodisulfides instead of the expected products - chlorosulfides.
