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Chemospecific and Regioselective Ethereal Methyl-Oxygen Bond Cleavage Behavior of Aroylated Dimethoxynaphthalenes by Combined Action of AlCl<sub>3</sub> and Aroyl Group
Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
Department of Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
Department of Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
- 1 Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
- 2 Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
- 3 Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
- 4 Department of Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
- 5 Department of Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan
International Journal of Organic Chemistry·Volume 02 (2012)·Pages 194–201·Published 25 September 2012·DOI10.4236/ijoc.2012.23029
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Abstract
AlCl 3 -mediated cleavage of ethereal methyl–oxygen bond in aroylated 2,7-dimethoxynaphthalene compounds proceeds chemospecifically and regioselectively. The ethereal bond at the β (2)-position of 1-monoaroylated 2,7-dimethoxynaphthalene is cleaved readily and predominantly against the β (7)-position, whereas scission of β -ethereal bonds of 1,8-diaroylated 2,7-dimethoxynaphthalene hardly undergoes like the non-aroylated mother frame compound of 2,7-dimethoxynaphthalene.
KeywordsAroylated 27-DialkoxynaphthaleneChemospecific and Regioselective Scission of Ethereal Alkyl–Oxygen BondCombined Action of AlCl<sub>3</sub>and Aroyl GroupNeighboring Group Effect
- Z. Furen, S. Haibin and Z. Guofu, “Synthesis and Catalytic Activity of Group 5 Metal Amides with Chiral Biaryl- diamine-Based Ligands,” Dalton Transactions, Vol. 40, No. 7, 2011, pp. 1547-1566. doi:10.1039/c0dt01229g
- J-P. Genet, “Asymmetric Catalytic Hydrogenation. Design of New Ru Catalysts and Chiral Ligands:? from Laboratory to Industrial Applications,” Accounts of Chemical Research, Vol. 36, No. 12, 2003, pp. 908-918. doi:10.1021/ar020152u
- O. Lucchi, “High Symmetry Chiral Auxiliaries Containing Heteroatoms,” Pure and Applied Chemistry, Vol. 68, No. 4, 1996, pp. 945-950. doi:10.1351/pac199668040945
- K. Maruoka, “Assymetric Phase Transfer Catalysis,” Wiley-VCH, Weinheim, 2008. doi:10.1002/9783527622627
- A. Okamoto and N. Yo-nezawa,“Reversible ArSE Aroyla tion of Naphthalene Derivatives,” Chemistry Letters, Vol. 38, No. 9, 2009, pp. 914-915. doi:10.1246/cl.2009.914
- A. Okamoto, R. Mitsui, H. Oike and N. Yonezawa, “Lewis Acid-Mediated ArSE Aroylation of Naphthalene Derivative: Distinct Second Aroylation Behavior of Naph- thyl Ketone,” Chemistry Letters, Vol. 40, No. 11, 2011, pp. 1283-1284. doi:10.1246/cl.2011.1283
- K. Nakaema, S. Watanabe, A. Okamoto, K. Noguchiand and N. Yonezawa, “1,8-Dibenzoyl-2,7-dimethoxynaphthalene,” Acta Crystallographica Section E, Vol. 64, No. 5, 2008, p. 807. doi:10.1107/S1600536808007009
- K. Sasagawa, T. Muto, A. Okamoto, H. Oikeand and N. Yonezawa, “[8-(4-Butoxybenzoyl)-2,7-dimethoxynaphtha- len-1-yl](4-butoxyphenyl)methanone,” Acta Crystallographica Section E, Vol. 67, No. 12, 2011, p. 3354. doi:10.1107/S1600536811048550
- T. Muto, K. Sasagawa, A. Okamoto, H. Oike and N. Yonezawa, “[8-(4-Chlorobenzoyl)-2,7-dimethoxynaphtha-len -1-yl](2,4,6-trimethylphenyl)methanone,” Acta Crystallo- graphica Section E, Vol. 68, No. 3, 2012, p. 906. doi:10.1107/S1600536812008112
- A. Okamoto, D. Hiji-kata, N. Sakai and N. Yonezawa, Polymer Journal, 2012, in press.
- T. W. Greene, “Protective Group in Organic Synthesis,” Wiley-Interscience, New York, 1991.
- M. De-muynck, P. D. Clercqand and M. Vandewalle, “(.+-.)-Hysterin: Revised Structure and Total Synthesis,” Journal of Organic Chemistry, Vol. 44, No. 26, 1979, pp. 4863-4866. doi:10.1021/jo00394a025
- H. Niwa, T. Hida and K. Yamada, “A New Method for Cleavage of Aliphatic Methyl Ethers,” Tetrahedron Letters, Vol. 22, No. 42, 1981, pp. 4239-4240. doi:10.1016/S0040-4039(01)82114-6