Accession Number : AD0610403

Title :   THE PHOTOCHEMICALLY INDUCED FRIES REARRANGEMENT OF AROMATIC ESTERS.

Descriptive Note : Rept. for 1 Jan 62-1 Sep 63,

Corporate Author : AIR FORCE MATERIALS LAB WRIGHT-PATTERSON AFB OHIO

Personal Author(s) : Mattice,James J.

Report Date : DEC 1964

Pagination or Media Count : 44

Abstract : This investigation involved aryl esters for which a photochemical rearrangement had not previously been reported. Results of the photolysis of eight aromatic benzoates (phenyl, p-tolyl, p-chlorophenyl, phenyl pchloro, 2,6-dimethylphenyl, mesityl, and phenyl mesitoate) are presented. Ortho- and para-hydroxybenzophenones are formed in cases where structural considerations permit, as well as products which, in certain instances, could not be identified. The photo-reaction has also been studied in two examples in the ferrocene series. An unexpected preference for formation of para-hydroxyketone is observed. The photo-Fries reactions investigated are discussed on the basis of the products formed and in comparison with related work in the current literature. Possible intermediates and mechanisms which might account for the observed reactions are pointed out and suggestions for future experimental work outlined. (Author)

Descriptors :   (*PHOTOCHEMICAL REACTIONS, AROMATIC COMPOUNDS), (*ESTERS, PHOTOCHEMICAL REACTIONS), BENZOATES, FERROCENES, MOLECULAR STRUCTURE, SOLVENTS, COATINGS

Distribution Statement : APPROVED FOR PUBLIC RELEASE