The Structure–Reactivity–Chemoselectivity Relationship on the Reactions of 1-Unsubstituted Tautomeric 2-Pyridones with Benzyne

Autor:	Akihiro Noguchi, Ei-ichi Mano, Takachiyo Okuda, Masayuki Kuzuya
Rok vydání:	1985
Předmět:	Chemistry Computational chemistry Stereochemistry Michael reaction Reactivity (chemistry) General Chemistry Chemical equilibrium Chemoselectivity Aryne Tautomer Adduct Diels–Alder reaction
Zdroj:	Bulletin of the Chemical Society of Japan. 58:1149-1155
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.58.1149
Popis:	The reactions of 2-pyridones with benzyne were investigated in order to gain some insight into the structure–reactivity–chemoselectivity relationship involved in the tautomeric systems. All reactions examined have resulted in the formation of Diels-Alder and Michael-type adducts. It has been shown that the Diels-Alder reactivities were well correlated with the HOMO energy levels of the 2-pyridone form and the yields of the Michael-type adduct were closely associated with the tautomeric equilibria. In summary, the chemoselectivities of 2-pyridones in the reaction with benzyne were largely affected by the tautomeric properties.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::89e2a888de990f307bf9c9458b396567 https://doi.org/10.1246/bcsj.58.1149 Zobrazit plný text záznamu