HYDROGEN ISOTOPE EFFECT IN THE AMINATION OF CHLOROBENZENE BY SODAMIDE
- 1 January 1961
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 39 (1) , 180-191
- https://doi.org/10.1139/v61-022
Abstract
Mixtures of chlorobenzene and chlorobenzene-2-2H have been subjected to partial amination by sodamide in liquid ammonia and both the unreacted starting material and the product aniline have been analyzed for deuterium. Deuterium in the aniline is distributed approximately equally between the ortho and meta positions. The results give strong support to the mechanism proposed by Roberts and co-workers in which the slow step is the formation of an intermediate, such as benzyne, which is symmetrical with respect to carbon atoms 1 and 2.Keywords
This publication has 10 references indexed in Scilit:
- STERIC INHIBITION OF A SECONDARY DEUTERIUM ISOTOPE EFFECT1Journal of the American Chemical Society, 1960
- Orientation in Aminations of Substituted Halobenzenes1Journal of the American Chemical Society, 1956
- The Deuteration of Aniline in the Presence of Raney AlloyJournal of the American Chemical Society, 1954
- REARRANGEMENT IN THE REACTION OF CHLOROBENZENE-1-C14 WITH POTASSIUM AMIDE1Journal of the American Chemical Society, 1953
- The Preparation of Aromatic Amines with Sodium Amide in Liquid AmmoniaJournal of the American Chemical Society, 1952
- Dibenzofuran. XXIII. Rearrangement of Halogen Compounds in Amination by Sodamide1Journal of the American Chemical Society, 1945
- DETERMINATION OF DEUTERIUM IN ORGANIC COMPOUNDSPublished by Elsevier ,1937
- THE ACTION OF BASES ON ORGANIC HALOGEN COMPOUNDS. I. THE REACTION OF ARYL HALIDES WITH POTASSIUM AMIDEThe Journal of Organic Chemistry, 1936
- A Rapid Catalytic Preparation of Sodamide in Liquid Ammonia and Some of its Uses in the Preparation of Acetylenic MaterialsJournal of the American Chemical Society, 1934
- A QUALITATIVE COLOR TEST FOR THE GRIGNARD REAGENTJournal of the American Chemical Society, 1925