On the scope of oxidation of tertiary amines: Meisenheimer rearrangements versus Cope elimination in 2-(cyanoethyl)-2-azanorbornanes

• Tipo: Artigo em Revista Científica Internacional
• Data: 2016

Autores

Sousa, CAD (Autor) Outra; Sampaio Dias, IE (Autor) Outra; Garcia Mera, X (Autor) Outra; Lima, CFRAC (Autor) FCUP; Rodriguez Borges, JE (Autor) FCUP

Revista

Título: Organic Chemistry Frontiers

Vol. 3

Páginas: 1624-1634

ISSN: 2052-4110

Editora: Royal Society of Chemistry

Indexação

ISI Web of Knowledge - 7 Citações

Scopus - 8 Citações

Outras Informações

ID Authenticus: P-00M-82V

DOI: 10.1039/c6qo00330c

Abstract (EN): In this work, rearrangement reactions subsequent to the oxidation of tertiary amines were studied in 2-(cyanoethyl)-2-azanorbornane/ene systems. [1,2]- and [2,3]-Meisenheimer rearrangements, as well as the Cope elimination reaction, were observed with virtually complete selectivity. It was found that 2-(cyanoethyl)-2-azanorbornanes afford N-hydroxylamines through Cope elimination reactions and 2-(cyanoethyl)-2-azanorbornenes are prone to Meisenheimer rearrangements. In addition, the endo/exo configuration of 2-azanorbornenes plays a key role in the Meisenheimer rearrangement outcome. All the synthesized compounds were fully characterized by NMR spectroscopy and HRMS.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11