Stereochemistry of Free-Radical Eliminations on β-Phenylsulfonyl Radicals
Tributyltin radicals have been allowed to react with erythro- and threo-2-bromo-3-(phenylsulfonyl)butane (5a,b) to generate β-(phenylsulfonyl)-sec-butyl radicals 9.The intermediate 9 eliminates phenylsulfonyl radicals to form 2-butenes in a nonstereospecific manner.The lack of stereospecificity is due to rotation about the C2-C3 bond before the loss of the phenylsulfonyl radical can occur and implies that the stabilization of the radical by sulfur bridging is negligible.
Boothe, Thomas E.,Greene, Joseph L.,Shevlin, Philip B.
p. 794 - 797
(2007/10/02)
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