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Pure Appl. Chem., 2001, Vol. 73, No. 3, pp. 529-534

http://dx.doi.org/10.1351/pac200173030529

Quinone methide intermediates in organic photochemistry

Peter Wan*, Darryl W. Brousmiche, Christy Z. Chen, John Cole, Matthew Lukeman and Musheng Xu

Department of Chemistry, Box 3065, University of Victoria, Victoria, British Columbia, V8W 3V6, Canada

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  • Ke Hua, Wang Li, Chen Yong, Lin Mei-Jin, Chen Jian-Zhong: Electron-deficient naphthalene diimides as efficient planar π-acid organocatalysts for selective oxidative C–C coupling of 2,6-di-tert-butylphenol: A temperature effect. Journal of Molecular Catalysis A: Chemical 2014, 385, 26. <http://dx.doi.org/10.1016/j.molcata.2014.01.014>
  • Basarić Nikola, Došlić Nađa, Ivković Jakov, Wang Yu-Hsuan, Veljković Jelena, Mlinarić-Majerski Kata, Wan Peter: Excited State Intramolecular Proton Transfer (ESIPT) from Phenol to Carbon in Selected Phenylnaphthols and Naphthylphenols. J. Org. Chem. 2013, 78, 1811. <http://dx.doi.org/10.1021/jo301456y>
  • Wang Yu-Hsuan, Wan Peter: Solvent-dependent excited state intramolecular proton transfer (ESIPT) pathways from phenol to carbon in 2,5-dihydroxyphenyl arenes. Photochem. Photobiol. Sci. 2013, 12, 1571. <http://dx.doi.org/10.1039/c3pp50091h>
  • Škalamera Đani, Mlinarić-Majerski Kata, Uzelac Lidija, Kralj Marijeta, Wan Peter, Basarić Nikola: Photosolvolysis of bulky (4-hydroxyphenyl)naphthalene derivatives. Photochem. Photobiol. Sci. 2013, 12, 2043. <http://dx.doi.org/10.1039/c3pp50190f>
  • Arumugam Selvanathan, Orski Sara V., Mbua Ngalle Eric, McNitt Christopher, Boons Geert-Jan, Locklin Jason, Popik Vladimir V.: Photo-click chemistry strategies for spatiotemporal control of metal-free ligation, labeling, and surface derivatization. Pure Appl. Chem. 2013, 1. <http://dx.doi.org/10.1351/PAC-CON-13-01-08>
  • Juhász Márta, Takahashi Seiji, Kitahara Yuki, Fujii Toshihiro: Thermal decomposition of pyridoxine: an evolved gas analysis-ion attachment mass spectrometry study. Rapid Commun. Mass Spectrom. 2012, 26, 759. <http://dx.doi.org/10.1002/rcm.6161>
  • Wilhelm-Mouton Anke, Bonnet Susan L., Ding Yuanqing, Li Xing-Cong, Ferreira Daneel, van der Westhuizen Jan H.: Photochemistry synthesis. Part 2: Enantiomerically pure polyhydroxy-1,1,3-triarylpropan-2-ols. J Photochem Photobiol A Chem 2012, 227, 18. <http://dx.doi.org/10.1016/j.jphotochem.2011.10.019>
  • Osyanin Vitalij A., Sidorina Natalia E., Klimochkin Yuri N.: Convenient Synthesis of 1H-Benzotriazolylalkylphenols. Synthetic Communications 2012, 42, 2639. <http://dx.doi.org/10.1080/00397911.2011.563452>
  • Wu Min, Xu Qi, Strid Åke, Martell Jaime M., Eriksson Leif A.: Theoretical Study of Pyridoxine (Vitamin B6) Photolysis. J Phys Chem A 2011, 115, 13556. <http://dx.doi.org/10.1021/jp205724k>
  • Wang Yu-Hsuan, Wan Peter: Excited state intramolecular proton transfer (ESIPT) in dihydroxyphenyl anthracenes. Photochem Photobiol Sci 2011, 10, 1934. <http://dx.doi.org/10.1039/c1pp05187c>
  • Basarić Nikola, Cindro Nikola, Hou Yunyan, Žabčić Ivana, Mlinarić-Majerski Kata, Wan Peter: Competing photodehydration and excited-state intramolecular proton transfer (ESIPT) in adamantyl derivatives of 2-phenylphenols. Can J Chem 2011, 89, 221. <http://dx.doi.org/10.1139/V10-102>
  • Wan Peter, Brousmiche Darryl W., Chen Christy Z., Cole John, Lukeman Matthew, Xu Musheng: ChemInform Abstract: Quinone Methide Intermediates in Organic Photochemistry. ChemInform 2010, 32, no. <http://dx.doi.org/10.1002/chin.200146286>
  • Basarić Nikola, Franco-Cea Alfredo, Alešković Marija, Mlinarić-Majerski Kata, Wan Peter: Photochemical deuterium exchange in phenyl-substituted pyrroles and indoles in CD3CN–D2O. Photochem Photobiol Sci 2010, 9, 779. <http://dx.doi.org/10.1039/b9pp00206e>
  • Ferreira Sabrina B., da Silva Fernando de C., Pinto Angelo C., Gonzaga Daniel T. G., Ferreira Vitor F.: Syntheses of chromenes and chromanes via o-quinone methide intermediates. J Heterocyclic Chem 2009, 46, 1080. <http://dx.doi.org/10.1002/jhet.232>
  • Arumugam Selvanathan, Popik Vladimir V.: Photochemical Generation and the Reactivity of o-Naphthoquinone Methides in Aqueous Solutions. J Am Chem Soc 2009, 131, 11892. <http://dx.doi.org/10.1021/ja9031924>
  • Patel Anjan, Netscher Thomas, Rosenau Thomas: Stabilization of ortho-quinone methides by a bis(sulfonium ylide) derived from 2,5-dihydroxy-[1,4]benzoquinone. Tetrahetron Lett 2008, 49, 2442. <http://dx.doi.org/10.1016/j.tetlet.2008.02.045>
  • Nayak Manoj Kumar, Wan Peter: Direct and water-mediated excited state intramolecular proton transfer (ESIPT) from phenol OH to carbon atoms of extended ortho-substituted biaryl systems. Photochem Photobiol Sci 2008, 7, 1544. <http://dx.doi.org/10.1039/b810111f>
  • Petrucci Rita, Astolfi Paola, Greci Lucedio, Firuzi Omidreza, Saso Luciano, Marrosu Giancarlo: A spectroelectrochemical and chemical study on oxidation of hydroxycinnamic acids in aprotic medium. Electrochimica Acta 2007, 52, 2461. <http://dx.doi.org/10.1016/j.electacta.2006.08.053>
  • Chacko Silvi A., Wenthold Paul G.: Dissociation of chloride from ortho-, meta- and para-chloromethylphenoxides: The enthalpy of formation of meta-quinomethane. Int J Mass Spectrosc 2007, 267, 277. <http://dx.doi.org/10.1016/j.ijms.2007.02.052>
  • Rayne Sierra, Eggers Nigel J.: 4-Ethylphenol and 4-ethylguaiacol in wines: Estimating non-microbial sourced contributions and toxicological considerations. Journal of Environmental Science and Health, Part B 2007, 42, 887. <http://dx.doi.org/10.1080/03601230701623365>
  • Kulkarni S. A., Moir D., Zhu J.: Influence of structural and functional modifications of selected genotoxic carcinogens on metabolism and mutagenicity – a review. SAR & QSAR in Env Res 2007, 18, 459. <http://dx.doi.org/10.1080/10629360701430090>
  • Lukeman Matthew, Veale Duane, Wan Peter, Munasinghe V Ranjit N., Corrie John ET: Photogeneration of 1,5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution. Can J Chem 2004, 82, 240. <http://dx.doi.org/10.1139/v03-184>