o-Fluoranil Chemistry: Diels–Alder versus Hetero-Diels–Alder Cycloaddition

The title quinone undergoes [4 + 2] cycloadditions in two ways, Diels–Alder on the ring and hetero-Diels–Alder by attack at the oxygens. The latter mode of reaction is strongly favored thermodynamically, but there is a kinetic bias favoring the normal Diels–Alder addition that often prevails, especi...

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Veröffentlicht in:	Journal of organic chemistry 2008-05, Vol.73 (9), p.3392-3396
Hauptverfasser:	Lemal, David M, Ramanathan, Sudharsanam, Shellito, John
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Kinetics and mechanisms Noncondensed benzenic compounds Organic chemistry Preparations and properties Reactivity and mechanisms
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	The title quinone undergoes [4 + 2] cycloadditions in two ways, Diels–Alder on the ring and hetero-Diels–Alder by attack at the oxygens. The latter mode of reaction is strongly favored thermodynamically, but there is a kinetic bias favoring the normal Diels–Alder addition that often prevails, especially with cycloaddends that are not electron-rich.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo7026678