Photo-reduction of chloro- and bromo-aromatic compounds

Pinhey, John T.; Rigby, R.D.G.

doi:10.1016/s0040-4039(01)87859-x

Cited by 59 publications

(23 citation statements)

References 8 publications

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“…The preferential loss of the chlorine from the 3position is consistent with a generally higher reactivity of chlorines 'ortho' to a substituent (Pinhey and Rigby, 1969;Davidson et al, 1984), which has been rationalized as a steric effect. Following loss of the chlorine, an aryl radical is formed which could either dimerize, abstract a hydrogen atom, or attack a reactive site such as an aromatic amino acid in a protein (leading to a photoadduct between protein and salicylanilide).…”

Section: Photochemical Transformations Of Tcsamentioning

confidence: 60%

Photochemical Transformations in Salicylanilide Photoallergy

Epling

Wells

Yoon

1988

Photochem & Photobiology

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The photochemical transformations of 3,3',4',5-tetrachlorosalicylanilide, have been characterized by isolation and spectroscopic determination of the primary and secondary photoproducts. The photoreactivity cleanly involves photochemical dechlorination; three chlorines are ultimately lost in an efficient stepwise fashion. A radical mechanism was implicated by formation of a dirner and hydrogen atom abstraction from cysteine when present during photolysis. In the presence of HSA or BSA. the initial dehalogenation leads to a photoadduct with the protein, but dehalogenation of the primary photoproduct. a trichloro compound, does no^ lead to an efficient photobinding to protein.

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Section: Photochemical Transformations Of Tcsamentioning

confidence: 60%

Photochemical Transformations in Salicylanilide Photoallergy

Epling

Wells

Yoon

1988

Photochem & Photobiology

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“…The photochemistry of halogenated aromatic compounds has recently received considerable attention (1)(2)(3)(4). Much of this interest stems from the widespread occurrence of aryl chlorides as environ-I mental contaminants (5, 6).…”

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confidence: 99%

The photolysis of chlorinated p-terphenyls

Chittim¹,

Safe²,

Bunce³

et al. 1978

Can. J. Chem.

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, LUIS 0 . RUZO, KARL OLIE, and O r r o HUTZINGER. Can. J. Chem. 56, 1253Chem. 56, (1978.A variety of chlorinated p-terphenyls was photolyzed in organic media a t 300 nm. Replacement of chlorine by hydrogen (dechlorination) was the major reaction. Substitution products were much more prominent than in the corresponding reactions of polychlorinated biphenyls.Quantum yields of reaction were substantially higher for ortho-chlorinated compounds. Xenon-assisted reactions and benzophenone sensitization indicate a triplet reactive state, although energy transfer from benzophenone is very inefficient. Triethylamine promoted an electron transfer pathway but only for those compounds that were least photolabile. On a effectuk la photolyse, dans des milieux organiques i 300 nm, d'un certain nombre de p-terphknyles chloris. La rtaction principale correspond a u remplacement du chlore par un hydrogene (dkchloration). Les produits de substitution sont beaucoup plus importants que dans les reactions correspondantes des biphenyles polychlorCs.Les rendements quantiques des reactions sont beaucoup plus Cleves pour les composCs ortl~o-chlores. Les reactions assistCes par le xenon ou par une sensibilisation par le benzophenone indiquent la presence d'un Btat reactif triplet quoique le transfert d'energie de la benzophenone est tres inefficace. La trikthylamine aide un chemin de transfert d'klectron mais uniquement pour les composts qui sont les moins photolabiles.[Traduit par le journal] I

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“…Until relatively recently (5), however, simple chloroarornatic compounds have not received much attention. The limited interest of photochemists in compounds of this type can perhaps be explained by the commonly held view that there is generally little cleavage of the C-Cl bond in chloroaromatic compounds (6).…”

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confidence: 99%