Photocatalytic alkoxylation of benzene with 3-cyano-1-methylquinolinium ion
作者： Kei Ohkubo , Takaki Kobayashi , Shunichi Fukuzumi
DOI: 10.1364/OE.20.00A360
关键词:
摘要: One-pot alkoxylation of benzene with alcohols occurs under photoirradiation 3-cyano-1-methylquinolinium ion in an oxygen-saturated acetonitrile solution containing and alcohols. The photocatalytic reaction mechanism was clarified by nanosecond laser flash photolysis. photocataytic is initiated photoinduced electron transfer from to the singlet excited state ion, followed nucleophilic addition radical cation. In case photoethoxylation, optimal product quantum yields ethoxybenzene were 20% 10%, respectively.
osapublishing.org
harvard.edu
researchgate.net 参考文章(19)
Toshihiko Maeyama, Naohiko Mikami, Intracluster ion-molecule reactions within the photoionized van der Waals complexes of C6H5F with NH3 and with H2O The Journal of Physical Chemistry. ,vol. 95, pp. 7197- 7204 ,(1991) , 10.1021/J100172A020
Detlef Thoelmann, Hans Friedrich Gruetzmacher, Reactions of dihalobenzene radical cations with ammonia in the gas phase. Reactivity pattern for nucleophilic aromatic substitution Journal of the American Chemical Society. ,vol. 113, pp. 3281- 3287 ,(1991) , 10.1021/JA00009A010
Toshihiko. Maeyama, Naohiko. Mikami, Nucleophilic substitution within the photoionized van der Waals complex: generation of C6H5NH3+ from C6H5Cl-NH3 Journal of the American Chemical Society. ,vol. 110, pp. 7238- 7239 ,(1988) , 10.1021/JA00229A062
Guy Bouchoux, Julien De Winter, Robert Flammang, Pascal Gerbaux, Aromatic substitution reactions between ionized benzene derivatives and neutral methyl isocyanide. Journal of Physical Chemistry A. ,vol. 114, pp. 7408- 7416 ,(2010) , 10.1021/JP102794C
Raffaele Molinari, Teresa Poerio, Remarks on studies for direct production of phenol in conventional and membrane reactors Asia-Pacific Journal of Chemical Engineering. ,vol. 5, pp. 191- 206 ,(2010) , 10.1002/APJ.369
Toshihiko. Maeyama, Naohiko. Mikami, Nucleophilic substitution within the photoionized van der Waals complex C6H5Cl-NH3 The Journal of Physical Chemistry. ,vol. 94, pp. 6973- 6977 ,(1990) , 10.1021/J100381A012
Enrico Baciocchi, Tiziana Del Giacco, Osvaldo Lanzalunga, Paolo Mencarelli, Barbara Procacci, Photosensitized oxidation of alkyl phenyl sulfoxides. C-S bond cleavage in alkyl phenyl sulfoxide radical cations. Journal of Organic Chemistry. ,vol. 73, pp. 5675- 5682 ,(2008) , 10.1021/JO801088N
Hiroto Tachikawa, Intramolecular SN2 reaction caused by photoionization of benzene chloride-NH3 complex: direct ab initio molecular dynamics study. Journal of Physical Chemistry A. ,vol. 110, pp. 153- 159 ,(2006) , 10.1021/JP0550659
Jack M. Miller, K. H. So, James H. Clark, Fluoride ion promoted synthesis of alkyl phenyl ethers Canadian Journal of Chemistry. ,vol. 57, pp. 1887- 1889 ,(1979) , 10.1139/V79-299
Hironori Kitaguchi, Kei Ohkubo, Seiji Ogo, Shunichi Fukuzumi, Electron-Transfer Oxidation Properties of Unsaturated Fatty Acids and Mechanistic Insight into Lipoxygenases Journal of Physical Chemistry A. ,vol. 110, pp. 1718- 1725 ,(2006) , 10.1021/JP054648F