59059-66-4Relevant articles and documents
Addition of Methanesulfonyl Radical to Alkenes and Alkenylsilanes
Gozdz, Antoni S,Maslak, Przemyslaw
, p. 2179 - 2189 (2007/10/02)
Relative reactivities of a series of olefins (alkenes, cycloalkenes, and alkenylsilanes) towards the electrophilic methanesulfonyl radical (2.) have been determined in acetonitrile at 0 deg C.A kinetic treatment of the competitive photoinitiated addition of methanesulfonyl bromide (1) to olefins was developed and used to measure the relative reactivity and probe the reversibility of addition.The kinetic treatment was based on the irreversible addition of 2. to a reference olefin serving as a standard reaction. 1,1-Dicyclopropylethene (14, a "radical clock") was used as such a primary reference, and 1-hexene and 1-octene were employed as secondary references. 14 was 20 +/- 4 times more reactive than 1-hexene, but the relative reactivites of several unactivated alkenes and alkenylsilanes vs 1-hexene were in a range from ca. 0.44 to 6.2.The absolute rate of addition of 2. to n-alkenes was estimated to be ca. one-tenth of the diffusion-limited rate.The study showed that, even within a family of closely related alkenes, steric and electronic effects gave significant influence on olefin reactivity toward 2. as well as reversibility of the addition.
Process for the production of bromo substituted tetrahydrofuran sulfones
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, (2008/06/13)
A process for the manufacture of β-bromoalkylsulfones and β-bromoalkenylsulfones by addition reaction of sulfonic acid bromides with olefins or acetylenes in the presence of hydroperoxide and, optionally, of metal salts. Starting materials for further syn
