Computational studies on the reactivity of substituted 1,2-dihydro-1,2-azaborines

Silva, Pedro J.; Ramos, Maria João

http://hdl.handle.net/10284/3293

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Authors

Silva, Pedro J.

Ramos, Maria João

Abstract(s)

We have investigated important intermediates of electrophilic aromatic substitution reactions and one-electron oxidation of substituted 1,2-dihydro-1,2-azaborines with density-functional theory. The results show that electrophilic substitution reactions and one-electron oxidation of substituted 1,2-azaborines are generally much more favorable than those of the corresponding benzene derivatives. Both chlorination and nitration of several boron-unsubstituted 1,2-azaborines are expected to break the boron−hydrogen bond, yielding boron-chlorinated 1,2-azaborines and a novel class of boron-bound 1,2-azaborinyl nitrites, respectively. Comparison between the relative stabilities of C3-bound and C5-bound Wheland intermediates of different electrophilic substitution reactions of 1,2-azaborines further suggests that the preference of the C3- over C5-substitution decreases with decreasing electrophilicity of the attacking group.

Keywords

1,2-azaborines Electrophilic aromatic substitution Density-functional theory Reactivity FeClз

URI

http://hdl.handle.net/10284/3293

Citation

Silva, Pedro J. e Ramos, Maria João (2009). Studies on the Reactivity of Substituted 1,2-Dihydro-1,2-azaborines. The Journal of Organic Chemistry, 74 (16), 6120-6129. DOI: 10.1021/jo900980d. ISSN 1520-6904.