Utilize este identificador para referenciar este registo: http://hdl.handle.net/10284/3293
Título: Computational Studies on the Reactivity of Substituted 1,2-Dihydro-1,2-azaborines
Autor: Silva, Pedro J.
Ramos, Maria João
Palavras-chave: 1,2-azaborines
Electrophilic aromatic substitution
Density-functional theory
Reactivity
FeCl3
Data: 2009
Editora: American Chemical Society
Citação: Journal of Organic Chemistry. ISSN 1520-6904. 74, 16 (2009) 6120–6129.
Relatório da Série N.º: Journal of Organic Chemistry;74, 16
Resumo: 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.
Peer review: yes
URI: http://hdl.handle.net/10284/3293
ISSN: 1520-6904
Versão do Editor: The definitive version is available at: http://pubs.acs.org/doi/abs/10.1021/jo900980d/ A versão definitiva está disponível em: http://pubs.acs.org/doi/abs/10.1021/jo900980d
Aparece nas colecções:FCS - Artigos em Revistas Científicas Internacionais com Arbitragem Científica

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