halogen compoundshalogen compounds (acyclic compounds) P 0030
-081Vinylic S N 2 Reaction of 1-Decenyliodonium Salt with Halide Ions.-Reactions of title compound (I) with tetrabutylammonium halides are examined under various conditions and the mechanistic details are investigated. In the present reaction system no sign of formation of the primary vinyl cation is found. In protic and aprotic solvents the main reaction pathway is the nucleophilic substitution with exclusive inversion, accompanied by an intramolecular β-elimination. The elimination becomes predominant with decreasing concentrations of the halide. According to the in-plane vinylic S N 2 mechanism the substitution products (II) are always Z-configurated, only in some polar acidic solvents small amounts of E-isomers are involved, due to ligand coupling. -(OKUYAMA, T.; TAKINO, T.; SATO, K.; OSHIMA, K.; IMAMURA, S.; YAMATAKA, H.; ASANO, T.; OCHIAI, M.; Bull. Chem.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.