NEW METABOLITES FROM THE MICROBIAL OXIDATION OF FLUORINATED AROMATIC-COMPOUNDS

m-Bromo-alpha,alpha,alpha-trifluorotoluene (1) and 1-bromo-2,3-difluor obenzene (4) were subjected to microbial oxidation by Pseudomonas puti da strain 39/D and the corresponding Escherichia coli recombinant micr oorganism (Strain JM109(pDTG601)), which express toluene dioxygenase. The absolute stereochemistry of the major oxidation products have been determined as pha,alpha,alpha-trifluoromethylcyclohexa-4,6-diene (2), and S,3S)-1-bromo-5,6-difluoro-2,3-dihydroxy-4,6-diene (5). The regio chemistry of a minor metabolite has been established as pha,alpha,alph a-trifluoromethylcyclohexa-1,5-diene (3). (C) 1998 Elsevier Science S. A. All rights reserved.