Excited-State Intramolecular Proton Transfer in o-Hydroxybiaryls: A New Route to Dihydroaromatic Compounds

An excited-state intramolecular proton transfer (ESIPT) from the phenol OH to the 7‘-carbon on the naphthyl ring in o-(1-naphthyl)phenol (3) and 1-(1‘-naphthyl)-2-naphthol (4) leads to efficient (Φ = 0.1−0.2) formation of the corresponding dihydrobenzoxanthenes (5 and 7) via quinone methide intermed...

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Veröffentlicht in:	Journal of the American Chemical Society 2003-02, Vol.125 (5), p.1164-1165
Hauptverfasser:	Lukeman, Matthew, Wan, Peter
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology General and physical chemistry Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	An excited-state intramolecular proton transfer (ESIPT) from the phenol OH to the 7‘-carbon on the naphthyl ring in o-(1-naphthyl)phenol (3) and 1-(1‘-naphthyl)-2-naphthol (4) leads to efficient (Φ = 0.1−0.2) formation of the corresponding dihydrobenzoxanthenes (5 and 7) via quinone methide intermediates. This new reaction represents a clean, efficient, and high-yielding route to benzoxanthenes and dihydrobenzoxanthenes. A related ESIPT of similar efficiency has been detected at the 2‘-aromatic position in these systems, by deuterium labeling studies.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja029376y