123707-30-2Relevant academic research and scientific papers
Radical Chain Cyclizations. The Light Induced Addition of Tosyl Iodide and Tosyl Bromide to Diallyl Ether
Serra, Armenio C.,Correa, Carlos M. M. da Silva
, p. 801 - 817 (2007/10/02)
Tosyl iodide (TsI) and tosyl bromide (TsBr) add quickly to diallyl ether under normal sunlight yielding cyclic tetrahydrofuran derivatives, 3-iodomethyl-4-p-tolylsulphonylmethyltetrahydrofuran (C-a) and 3-bromomethyl-4-p-tolylsulphonylmethyltetrahydrofuran (C-b), and, in the case of tosyl iodide, the monoadduct, 2-iodo-3-(propen-2-yloxy)-1-p-tolylsulphonylpropane (MA-a) and the bisadduct, bis(2-iodo-3-p-tolylsulphonyl)ether (BA).No six member ring products were detected in the reaction mixtures.The reaction with tosyl iodide is very fast and can be ajusted (concentrations and molar ratios) to allow the isolation of either (MA-a) or (BA-a) or (C-a).The reaction with tosyl bromide is slower but the yield of cyclic adduct is higher.Tosyl iodide gave the cis-cyclic adduct only, while tosyl bromide yielded 15-20percent of the trans-cyclic adduct.These results are explained on the basis of the faster propagation step in the radical addition of TsI.
