51989-38-9Relevant academic research and scientific papers
INSERION REACTIONS OF DIAZO COMPOUNDS WITH SOME SELENIUM(II) ELECTROPHILES
Back, Thomas G.,Kerr, Russell G.
, p. 171 - 182 (1985)
Benzene- and o-nitrobenzene-selenyl thiocyanate (1 and 2) reacted with diazomethane and several α-diazo esters to afford α-arylseleno isothiocyanates (5a-10a) and the isomeric thiocyanates (6b-8b) as the major and minor products, respectively.Analogous insertion reactions were observed with benzenesulfenyl thiocyanate (3) and benzeneselenenyl selenocyanate (4) to furnish phenylthiomethyl isothiocyanate (11), ethyl α-phenylthioisocyanoacetate (12) and phenylselenomethyl isoselelnocyanate (13), ethyl α-phenylseleno-α-isoselenocyanoacetate (14), respectively.N-(Phenylseleno)phthalimide formed insertion products N-(phenylselenomethyl)phthalimide (16) and ethyl α-phenylseleno-α-phthalimidoacetate (17)with diazomethane and ethyl diazoacetate, but effected elimination to the corresponding vinyl selenides, ethyl α-(phenylseleno)propenoate (18) and ethyl 2-phenylseleno-3-methyl-2-butenoate (19) when treated with diazo esters containing β-hydrogens.Compound 19 was similarly obtained from benzeneselenenyl iodide and the diazo ester.Attempts to effect selenoxide eliminations in compounds 7a-10a were unsuccessful.A new, efficient preparation of 1 from the metathesis of benzeneselenenyl chloride with trimethylsilyl isothiocyanate was developed.
Chloro(phenylthio)methyltrimethylsilane: Preparation and some Synthetic Reactions
Yamamoto, Iwao,Okuda, Kazuhide,Nagai, Shigemasa,Motoyoshiya, Jiro,Gotoh, Haruo,Matsuzaki, Kei
, p. 435 - 438 (2007/10/02)
Reaction of the title compound (2) with lead thiocyanate gave phenylthio(trimethylsilyl)methyl isothiocyanate (3) which further reacted with aromatic aldehydes in the presence of fluoride ion to afford oxazoles in good yields.Compound (2) also reacted with silyl enol ethers to give β-silyl ketones which were capable of being converted into β-functionalized vinylsilanes.
