Accession Number : AD0666257

Title :   MECHANISM OF THE DECOMPOSITION OF IMIDOYL HALIDES.

Descriptive Note : Final rept.,

Corporate Author : CLEMSON UNIV S C

Personal Author(s) : Marullo,Nicasio P.

Report Date : FEB 1968

Pagination or Media Count : 45

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)

Descriptors :   (*IMINES, PYROLYSIS), CHLORINE COMPOUNDS, STEREOCHEMISTRY, MOLECULAR ROTATION, REACTION KINETICS, DECOMPOSITION, CHEMICAL BONDS

Subject Categories : Organic Chemistry
      Atomic and Molecular Physics and Spectroscopy

Distribution Statement : APPROVED FOR PUBLIC RELEASE