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ChemInform Abstract: Vinylic SN2 Reaction of 1-Decenyliodonium Salt with Halide Ions.

โœ Scribed by T. OKUYAMA; T. TAKINO; K. SATO; K. OSHIMA; S. IMAMURA; H. YAMATAKA; T. ASANO; M. OCHIAI

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
29
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Vinylic 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 ฮฒ-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.

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โœ Luisa M. Ferreira; Ana M. Lobo; Sundaresan Prabhakar; Antonieta C. Teixeira ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 29 KB ๐Ÿ‘ 1 views

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