MECHANISMS OF ELIMINATION REACTIONS. IV. DEUTERIUM ISOTOPE EFFECTS IN E2 REACTIONS OF SOME 2-PHENYLETHYL DERIVATIVES
Kinetic deuterium isotope effects were determined for E2 reactions of the compounds C/sub 6/H/sub 5/CD/sub 2/CH/sub 2/X. The values of k/sub H//k/sub D/ with sodium ethoxide in ethanol are in the order Br> OTs> SMe/sub 2/> NMe/sub 3/. A change of base and medium to potassium t-butoxide in t-butyl alcohol increases the isotope effect with the bromide and the tosylate. Experiments with sodium hydroxide in water on the onium salts show no clear pattern. The relation of the present work to other recent studies on the nature of the transition state in E2 reactions is discussed. Some rate constants previously given for 2-(p- acetylphenyl)-ethyldimethylsulfonium bromide are shown to be tn error. An interesting case of anomalous orientation in a Friedel-Crafts acylation is reported. (auth)
- Research Organization:
- Univ. of Rochester, N.Y.
- NSA Number:
- NSA-14-007342
- OSTI ID:
- 4176544
- Journal Information:
- Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Journal Issue: 1 Vol. Vol: 82; ISSN JACSA
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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Related Subjects
ALCOHOLS
ALUMINUM CHLORIDES
BROMIDES
BUTANOL
BUTOXIDES
CATALYSIS
CHEMICAL REACTIONS
CHEMISTRY
DEUTERIUM
DEUTERIUM COMPOUNDS
ETHANOL
ETHOXIDES
ETHYL RADICALS
FRIEDEL-CRAFT REACTION
ISOTOPE EFFECTS
METHYL RADICALS
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
PESB
PHENYL RADICALS
POTASSIUM OXIDES
REACTION KINETICS
SEPARATION PROCESSES
SODIUM HYDROXIDES
SODIUM OXIDES
SOLUTIONS
SULFONIC ACIDS
WATER