Accession Number : AD0476265


Title :   REACTION OF DIISONITROSOACETONE WITH SULFONYL CHLORIDES.


Descriptive Note : Quarterly rept. no. 1, Jul-Sep 65,


Corporate Author : DELAWARE UNIV NEWARK


Personal Author(s) : Mosher, William A


Report Date : 25 Oct 1965


Pagination or Media Count : 52


Abstract : This report embodies results of a mechanistic study of the color-forming reaction between 1,3-diisonitrosoacetone (DIA) and arylsulfonyl halides. It also includes considerable information about DIA itself. In contradiction of earlier workers, it was concluded that the usual preparative method yields a single symmetrical isomer of DIA. The syn-syn is favored over the anti-anti form, but it is emphasized that the question remains open. The high-resolution IR and NMR spectra of DIA and of DIA-dsub2, as well as ultraviolet spectral data are reported. Data on distribution coefficients, ionization constants, and polarography are set forth and discussed. Study of the color-forming reaction required spectroscopic (e.s.r., n.m.r., UV) measurements in aqueous media because the unstable product or products could not be isolated by solvent extraction. The investigators do not know the mechanism in detail but believe a numer of intermediates and competing processes are involved. A tentative reaction sequence is suggested. Free radicals were detected in this reaction; probably a single radical species is involved. Although a structure cannot be drawn for the radical at this stage of the investigation, high-resolution e.s.r. (electron spin resonance) spectroscopy has given considerable insight into its structural features. (Author)


Descriptors :   *BENZENE , *ACETONES , REACTION KINETICS , SOLUBILITY , ORGANIC SULFUR COMPOUNDS , OXYGEN COMPOUNDS , CHLORINE COMPOUNDS , OXIMES , MOLECULAR ISOMERISM , STEREOCHEMISTRY , NUCLEAR MAGNETIC RESONANCE , ULTRAVIOLET SPECTRA , VISIBLE SPECTRA , INFRARED SPECTRA , DISSOCIATION , FREE RADICALS , POLAROGRAPHIC ANALYSIS , WATER , ETHYL ETHERS , BUTANOLS , BUTANONES , ELECTRON PARAMAGNETIC RESONANCE , DEUTERIUM COMPOUNDS , HYPERFINE STRUCTURE , COLORS , PRODUCTION , DEGRADATION , HYDROLYSIS , SYNTHESIS(CHEMISTRY)


Subject Categories : Organic Chemistry
      Atomic and Molecular Physics and Spectroscopy


Distribution Statement : APPROVED FOR PUBLIC RELEASE