Nucleophilic Substitution of 1-Yhenyl-2-Phenyl Telluropropane to Yield 2-Halo-1-Phenylpropanes

Fumio Ogura Department of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University, Umenobe-1, Takaya, Higashi-Hiroshima, 739-2116, Japan

Yoshiharu Okada Department of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University, Umenobe-1, Takaya, Higashi-Hiroshima, 739-2116, Japan

Naoko Nishimura Department of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University, Umenobe-1, Takaya, Higashi-Hiroshima, 739-2116, Japan

Kenichiro Hamamoto Department of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University, Umenobe-1, Takaya, Higashi-Hiroshima, 739-2116, Japan

Makoto Miyakawa Department of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University, Umenobe-1, Takaya, Higashi-Hiroshima, 739-2116, Japan

Tetsuo Otsubo Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, 1-4-1, Kagamiyama, Higashi-Hiroshima, 739-8527, Japan

Yoshio Aso Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, 1-4-1, Kagamiyama, Higashi-Hiroshima, 739-8527, Japan

Shinobu Inoue Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, 1-4-1, Kagamiyama, Higashi-Hiroshima, 739-8527, Japan

Koji Tsutsui Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, 1-4-1, Kagamiyama, Higashi-Hiroshima, 739-8527, Japan

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Abstract

Mechanism of a novel transformation of the alkyl phenyltellurides to alkyl halides via nucleophilic substitution of the phenyltelluro group in organotelluriums is studied on the basis of kinetics and stereochemistry using the titled chiral substrate. The results obtained strongly suggest that the substitutions proceed via S_N2 mechanism with Walden inversion and very low Arrhenius' energies of activation.

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Nucleophilic Substitution of 1-Yhenyl-2-Phenyl Telluropropane to Yield 2-Halo-1-Phenylpropanes

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Nucleophilic Substitution of 1-Yhenyl-2-Phenyl Telluropropane to Yield 2-Halo-1-Phenylpropanes

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