Abstract
The addition of 2-nitro- and 2,4-dinitrobenzenesulfenyl chlorides in AcOH and under “doping conditions” (AcOH + LiClO4) to the olefins 8-10 has been investigated, and novel types of Wagner-Meerwein rearrangement have been found. The product distributions as well as the different configurations of rearranged chlorides (e.g., 18c) and acetates (e.g., 18d) were explained in terms of an ion-pair mechanism. Doping addition leads in part to the formation of covalent perchlorates (e.g., 12d,e), which have been isolated and identified. The general mechanistic features and stereochemical sequence for the ion-pair mechanism of ArSCl addition to a carbon-carbon double bond are discussed.
Original language | English (US) |
---|---|
Pages (from-to) | 5264-5275 |
Number of pages | 12 |
Journal | Journal of Organic Chemistry |
Volume | 46 |
Issue number | 26 |
DOIs | |
State | Published - Dec 1981 |