32291-91-1Relevant academic research and scientific papers
Silver(I)-mediated reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides: Unexpected formation of vinyl sulfones
Deng, Gui Sheng,Sun, Teng Fei
, p. 1115 - 1118,4 (2020/08/20)
A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yields and with Z-selectivity. A free radical mechanism has been proposed to account for the formation of the products.
Addition of Arenesulphonyl Iodides to Substituted Phenylacetylenes
Silva Correa, Carlos M. M. da,Fleming, Maria Daniela C. M.
, p. 103 - 108 (2007/10/02)
The products of the addition of toluene-p-sulphonyl iodide to substituted phenylacetylenes (and styrenes) are studied.The regiospecificity and stereoselectivity of trans addition to acetylenes is inferred from (1)H n.m.r. spectroscopy.The effect of substituents on the reactivity of substituted phenylacetylenes towards substituted beenzenesulphonyl radicals generated by photolysis of sulphonyl iodides is studied.Phenylacetylenes with electron-donating substituents react faster.Relative reactivities yield good Hammet-Brown correlations showing the electrophilic character of sulphonyl radicals towards phenylacetylenes.The selectivity of the addition (measured by ρ) of different sulphonyl radicals towards the same set of acetylenes ranges from -0.53 to -0.93 and shows a tendency to be smaller for benzenesulphonyl iodides carrying electron donating substituents.Results are discussed in terms of polar effects on the transition state and frontier molecular orbital theory.
