Projects / Programmes
Reactive Intermediates in Oxidation Reactions
January 1, 1999
- December 31, 2003
Code |
Science |
Field |
Subfield |
1.04.00 |
Natural sciences and mathematics |
Chemistry |
|
Code |
Science |
Field |
P003 |
Natural sciences and mathematics |
Chemistry |
P390 |
Natural sciences and mathematics |
Organic chemistry |
P305 |
Natural sciences and mathematics |
Environmental chemistry |
Researchers (8)
Organisations (1)
Abstract
Our long-term research goal is to provide new information on the synthesis, structure, and reactivity of a) alkyl hydrotrioxides (ROOOH), i.e., reactive intermediates formed in the low-temperature ozonation of various saturated organic substrates (hydrocarbons, alcohols, ethers, silanes, germanes), b) dialkyl trioxides (ROOOR), and c) hydrogen trioxide (HOOOH), which has been synthesized and characterized for the first time recently in our laboratory. We plan to continue our studies on iodanyl radicals (R-I-R), which are formed in the decomposition of various (alkylperoxy)- iodanes. The application of the desyl or 2-oxo-1,2-diphenylethyl moiety as a photolabile ligand for the release of phosphates, carboxylic acids, amino acids and nucleotides are becoming increasingly important research tools for introduction of reagents with precise spatial and temporal control. The synthesis and photochemical studies of fluoro substituted N- and O-desyl-caged versions of bioactive substances prepared from 2-chloro- (or bromo-) 2-fluoro-1-oxo-1,2-diphenyl- ethanes will be studied. Polycyclic aromatic hydrocarbons are widespread environmental pollutants. Benzo?a?pyrene can be metabolised into four isomers of diol epoxides, the (+)-(7R,8S)-diol-(9S,10R)epoxide predominates and has the most pronounced tumorigenicity. The vicinal hydroxy groups normally prefer the quasi-diequatorial orientation. Introduction of fluorine at position 6 of pyrene, which is peri to the benzylic hydroxyl, causes a conformational change of the angular tetrahydro ring and 6-fluoro analogue has no tumorigenic activity. Previously, two of the four possible isomeric diol epoxides of 6-fluorobenzo?a?pyrene were synthesized from the metabolically formed trans-(7R,8R)-dihydrodiol by known chemical methods. However, for structure-biology studies through DNA bonding, a convenient chemical synthesis that provides both the antipodes of the dihydrodiol and all from diol epoxides will be prepared.
Most important scientific results
Final report
Most important socioeconomically and culturally relevant results
Final report