113791-95-0Relevant academic research and scientific papers
Reaction of the system arene(hetarene)thiol-diselenide with phenylacetylene
Papernaya,Albanov,Sukhomazova,Levanova,Deryagina
, p. 708 - 712 (2004)
Liquid-phase thermal reactions of phenylacetylene with the system arene(hetarene)thioldiselenide at 110-180°C proceed through conjugate addition to the phenylacetylene triple bond of one alkylselanyl and one arene(hetarenesulfanyl groups to form 2-alkylse
Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient β-Sulfanylvinyl Radicals
Benati, Luisa,Capella, Laura,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 7941 - 7946 (2007/10/03)
The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzofuran-, and 2-benzothiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 deg C in the presence of AIBN and at room temperature in the presence of BEt3/O2.Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzofuranthiol failed to react with either alkyne in the presence of BEt3/O2 and unexpectedely gave 2-(ethylsulfanyl)benzofuran to a significant extent.The produced 2-(2-heteroarylsulfanyl)vinyl radicals largely preffered to undergo intramolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent.The 2-- and, especially, 2-vinyl radicals, besides H-abstraction, promptly underwent intramolecular 5-exo cyclization to give spiro radicals that interestingly underwent β-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group.The 2-vinyl radicals did not exhibit any similar 5-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.
LIQUID-PHASE THERMAL CONDENSATION OF AROMATIC AND HETEROAROMATIC THIOLS WITH β-CHLORO- AND β-BROMOSTYRENE
Kuznetsova, M. A.,Korchevin, N. A.,Deryagina, E. N.,Voronkov, M. G.
, p. 1136 - 1140 (2007/10/02)
Aromatic thiols and 2-thiophenethiol react with β-chloro- and β-bromostyrene when heated to form the corresponding 1-phenyl-2-aryl(thienyl)thioethenes.The reaction begins at 80 deg C and takes place effectively and strictly stereospecifically at 140-160 deg C.The yield of the respective vinyl sulfides amounts to 70-95percent. β-Bromostyrene reacts with thiophenol more slowly than β-chlorostyrene,and this is due to the inhibiting action of the hydrogen bromide, which acts as a trap for the thiyl radicals and gives rise to decomposition of the obtained 1-phenyl-2-phenylthioethene.A mong the investigated thiols 2-thiophenethiol has the lowest reactivity.
