MECHANISM OF THE DECOMPOSITION OF IMIDOYL HALIDES.
Abstract
The mechanistic properties of the decomposition of imino chlorides were studied by means of stereochemical and kinetic measurements. A stereochemical study was undertaken employing optically active N-alpha-phenethyl-substituted benzimino chlorides. These imino chlorides were not isolated but pyrolyzed in situ on preparation from the corresponding amide and chlorinating agent. The effect of electron withdrawing and donating groups on the extent of inversion of configuration in the resultant alpha-phenethyl chloride was determined. The influence of solvents and chlorinating agent (thionyl chloride or phosphorus pentachloride) on the stereochemistry of the product was also examined. A kinetic study was also undertaken employing N-alpha-p-nitrophenethylbenzimino chlorides. These imino chlorides were isolable, and were decomposed by heating in the appropriate solvent. The effect of electron withdrawing and donating groups was measured by their effect on the rate of decomposition. The effects of variations in temperature and solvent polarity were also investigated. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 01, 1968
- Accession Number
- AD0666257
Entities
People
- Nicasio P. Marullo
Organizations
- Clemson University