ChemInform Abstract: 6π/10π-Electrocyclization of Ketene-iminium Salts for the Synthesis of Substituted Naphthylamines

Autor:	Saron Catak, Didier Zurwerra, Roman Staiger, Emmanuelle Villedieu-Percheron, Alain De Mesmaeker, Mathilde Lachia
Rok vydání:	2014
Předmět:	Exergonic reaction Olefin fiber chemistry.chemical_compound Chemistry Intramolecular force Iminium Organic chemistry chemistry.chemical_element Ketene General Medicine Ring (chemistry) Medicinal chemistry Nitrogen
Zdroj:	ChemInform. 45
ISSN:	0931-7597
DOI:	10.1002/chin.201438092
Popis:	An intramolecular 6π/10π-electrocyclization from ketene-iminium salts was developed for the preparation of naphthylamines. Various substituents on the nitrogen, on the aromatic ring, and on the olefin were studied. Tricyclic skeletons were obtained in few steps and good overall yields. The electrocyclization of ketene-iminium salts has been computationally explored by means of DFT calculations and their activation barriers were compared to the parent triene as well as the corresponding dienyl allenes and dienyl ketenes. Electrocyclizations for ketene-iminium salts were shown to be highly exergonic and have much smaller barriers to activation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4c25050185197073a0ad3aecf1913638 https://doi.org/10.1002/chin.201438092 Zobrazit plný text záznamu Plný text