Magnetic isotope and external magnetic field effects upon the photo-Fries rearrangement of 1-naphthyl acetate

R Nakagaki, M Hiramatsu, T Watanabe…

Index: Nakagaki, Ryoichi; Hiramatsu, Mitsuo; Watanabe, Takeshi; Tanimoto, Yoshifumi; Nagakura, Saburo Journal of Physical Chemistry, 1985 , vol. 89, # 15 p. 3222 - 3226

Full Text: HTML

Citation Number: 67

Abstract

The reaction mechanism of the photo-Fries rearrangement of 1-naphthyl acetate has been studied by means of steady-state photolysis and laser flash photolysis. A radical pair consisting of the 1-naphthoxyl and acetyl radicals is concluded to be a reaction intermediate. The yield of an in-cage product (2-acetyl-1-naphthol) exhibits a positive external magnetic field effect for the ester labeled by magnetically active I3C, but no effect for the normal 12C ...

Related Articles:

Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: …

[Murashige, Ryo; Hayashi, Yuka; Ohmori, Syo; Torii, Ayuko; Aizu, Yoko; Muto, Yasuyuki; Murai, Yuta; Oda, Yuji; Hashimoto, Makoto Tetrahedron, 2011 , vol. 67, # 3 p. 641 - 649]

Thiol-selective fluorogenic probes for labeling and release

[Allen, Anna; Le Marquand, Paul; Burton, Ryan; Villeneuve, Karine; Tam, William Journal of Organic Chemistry, 2007 , vol. 72, # 21 p. 7849 - 7857]

The anticonvulsant activities of some substituted acetonaphthones

[Hunter,W.H. et al. Journal of Medicinal Chemistry, 1964 , vol. 7, p. 167 - 174]

The Fries Reaction with α-Naphthol Esters1, 2

[Stoughton Journal of the American Chemical Society, 1935 , vol. 57, p. 202]

Photogeneration of 1, 5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in …

[Lukeman, Matthew; Veale, Duane; Wan, Peter; Munasinghe, V. Ranjit N.; Corrie, John E.T. Canadian Journal of Chemistry, 2004 , vol. 82, # 2 p. 240 - 253]

More Articles...