OXIDATIVE STUDIES OF POLYPHENOLS.
Abstract
The primary purpose was to apply electrolytic techniques to quinone and hydroquinone systems to help elucidate the autoxidation process for the latter. Special conditions must be observed to detect free radicals formed by electrolytic oxidation of hydroquinones, but quinones are readily reduced to semiquinones in a number to solvents; seldom did subsidiary lines appear in the spectra that cannot be attributed to a semiquinone. Evidence is presented that variation of proton splitting constants for semiquinones is due primarily to H bonding in protic solvents. Investigation of the system of diprotonated semiquinone cations in concentrated H2SO4 showed that some quinones are apparently reduced to di-protonated semiquinone cations in 96-98% H2SO4, i.e. no additional reducing agent is necessary. The reaction of trivalent titanium ion with H202 was used to generate primary radicals that can be used to abstract H atoms from organic molecules, thereby generating free radicals that would be difficult to produce otherwise. Preliminary observations are made on the free radicals formed from quinones and the Lewis acids aluminum chloride and boron trifluoride.
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 01, 1965
- Accession Number
- AD0624875
Entities
People
- John E. Wertz
- John W. Thomas
Organizations
- University of Minnesota