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

• Type: Article in International Scientific Journal
• Date: 2016

Authors

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

Journal

Title: Organic Chemistry Frontiers

Vol. 3

Pages: 1624-1634

ISSN: 2052-4110

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 7 Citations

Scopus - 8 Citations

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 11