Differential photohydrodehalogenation reactivity of bromobenzenes (1,2,4-tribromobenzene, 1,2,3,5-tetrabromobenzene) and pentachlorobenzene: sunlight-based remediation.
The photochemical dehalogenation of 1,2,4-tribromobenzene, 1,2,3,5-tetrabromobenzene and pentachlorobenzene in open-air solutions of acetonitrile using natural and artificial sunlight as the irradiation source has been investigated. The regiochemistry of mono-dehalogenation has been determined for 1,2,4-tribromobenzene and 1,2,3,5-tetrabromobenzene. Pentachlorobenzene did not react. 1,2,4-Tribromobenzene yielded three products, 1,4-dibromobenzene, 1,3-dibromobenzene and 1,2-dibromobenzene with isomer percentages of 52 +/- 1%, 39 +/- 2% and 9 +/- 1%, respectively. 1,2,3,5-Tetrabromobenzene yielded 1,3,5-tribromobenzene, 1,2,4-tribromobenzene and 1,2,3-tribromobenzene with relative product percentages of 60 +/- 2%, 29 +/- 2%, 11 +/- 1%.
Freeman
P K
PK
Department of Chemistry, Oregon State University, Corvallis 97331, USA.
Haugen
C M
CM
D001673:Biodegradation, Environmental; D001709:Biotechnology / Q000379:methods; D001969:Bromobenzenes / Q000737:chemistry*; D002722:Chlorobenzenes / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007306:Insecticides / Q000737:chemistry*; D007700:Kinetics; D010777:Photochemistry; D013472:Sunlight
D001969:Bromobenzenes; D002722:Chlorobenzenes; D006219:Halogens; D007306:Insecticides; C026924:1,2,4-tribromobenzene; D006859:Hydrogen; C003060:pentachlorobenzene