Safety of 3-Bromo-4-chloronitrobenzene. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Singlet/triplet phenyl cations and benzyne from the photodehalogenation of some silylated and stannylated phenyl halides. Author is Protti, Stefano; Dichiarante, Valentina; Dondi, Daniele; Fagnoni, Maurizio; Albini, Angelo.
The photodehalogenation of fluoro- or chlorobenzene derivatives smoothly generates triplet and singlet Ph cations (3,1Ar+) and potentially benzyne. These intermediates lead to different products, which warrants exploring the direct effect of substituents. SiMe3 and SnMe3 groups have been found to be convenient probes since they affect neither the photophysics nor the primary dehalogenation of 4-chloroanisole and 4-chloro- (or 4-fluoro-) N,N-dimethylaniline (except for the case of 4-fluoro-3-(trimethylstannyl)aniline, which was preferentially demetallated). The stabilization by these groups (with SnMe3 ca. 10 kcal mol-1 for the triplets and 20 kcal mol-1 for the singlets, as computed by using (U)B3LYP DFT method with LANL2DZ basis set) made 1Ar+ the lowest state with stannylated and silylated anisoles and solvolysis the main process. On the other hand, donating substituents and an acidic solvent favored the triplet cation chem., a quite general process leading to reduction or (in the presence of π bond nucleophiles) to arylation. Noteworthily, the stannylated 4-N,N-dimethylaminophenyl cation eliminated the Me3Sn+ group, opening an unprecedented path to the corresponding benzyne. Apart from the control of the chem. output, the photostabilizing effect found with a silyl group may be useful for designing less phototoxic fluorinated drugs.
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