79618-79-4Relevant academic research and scientific papers
PARTICIPATION OF THE ClO4(1-) ANION IN ADDITION REACTIONS OF ArSCl AND HALOGENS WITH UNSATURATED DERIVATIVES OF TRICYCLO2,5>DECANE. SYNTHESIS OF STABLE COVALENT PERCHLORATES
Zefirov, N. S.,Koz'min, A. S.,Zhdankin, V. V.
, p. 291 - 300 (2007/10/02)
New reactions, halogenoperchloration and arylsulfenylperchloration of olefins of the tricyclo2,5>decane series are described.Stable covalent perchlorates have been isolated in pure form in these reactions.Some important mechanistic and
Electrophilic Addition of Arylsulfenyl Chlorides to Tricyclo2,5>deca-3,7-diene and -3,7,9-triene Systems. Novel Skeletal Rearrangements and Serendipitous Products
Zefirov, Nikolai S.,Koz'min, Anatoly S.,Kirin, Valery N.,Zhdankin, Viktor V.,Caple, Ronald
, p. 5264 - 5275 (2007/10/02)
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.
