77657-92-2Relevant academic research and scientific papers
Neighboring Group Participation in the Oxidation of Hydroxy Sulfides. Control of the Reaction Courses and Products
Ueno, Yoshio,Miyano, Tadaaki,Okawara, Makoto
, p. 3615 - 3618 (2007/10/02)
Oxidation of the hydroxy sulfides with hexabutyldistannoxane (HBD)-bromine system was studied in order to clarify neighboring group participation during the course of reaction.The oxidation products were found to be highly dependent on
Stereochemistry of Free-Radical Eliminations on β-Phenylsulfonyl Radicals
Boothe, Thomas E.,Greene, Joseph L.,Shevlin, Philip B.
, p. 794 - 797 (2007/10/02)
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.
