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Original Articles

Tetrahydronaphthalene Derivatives by Amberlyst® 15-Promoted Friedel-Crafts Cyclizations

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Pages 83-93 | Received 28 Aug 2009, Accepted 01 Oct 2009, Published online: 03 Feb 2010

References

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  • 1978 . Amberlyst®15 Synthetic Resin Catalyst, Technical Bulletin—Fluid Process Chemicals , Philadelphia , PA : Rohm and Haas Company, Inc. .
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  • Acids 1 and 3 are commercially available . 1936 . Acid 2 was prepared from 4-chlorobenzoylpropanoic acid using the method developed by E. L. Martin . J. Am. Chem. Soc. , 58 : 1438 described in L. F. Fieser and M. Fieser, Reagents for Organic Synthesis, 1, 1287 (1967).
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  • Benzene was generally used as the solvent for this study, but heptane also gave excellent results, see , Bunce , R. A. and Reeves , H. D. 1990 . J. Chem Educ. , 67 : 69 It is likely that any unreactive hydrocarbon with a bp > 80°C can be used for this reaction
  • “ Since alkenes 16b–18b could not be isolated in pure form, and longer reaction times (8 h) cleanly converted them to 1,1-diphenyl-1,2,3,4-tetrahydronaphthalenes 12b–14b, they were not fully characterized ” .
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  • This compound has been previously reported, but detailed spectral data were not given, see , Sugimori , M. , Ejima , A. , Ohsuki , S. , Uoto , K. , Mitsui , K. , Kawato , Y. , Hirota , Y. , Sato , K. and Terasawa , H. 1998 . J. Med. Chem. , 41 : 2308
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  • “ This compound has been previously reported, but detailed spectral data were not given, see ref 6 ” .
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  • This compound has been previously reported, but detailed spectral data were not given. Partial spectral data were reported in ref 6 and in , Meyer , W. L. , Brannon , M. J. , Burgos , C. G. , Goodwin , T. E. and Howard , R. W. 1985 . J. Org. Chem. , 50 : 438
  • This compound has been previously reported but no spectral data were available, see , Braude , E. A. , Jackman , L. M. , Linstead , R. P. and Lowe , G. 1960 . J. Chem. Soc. , : 3123 A more recent paper had matching spectral data, but the reported mp was 93–95°C, see B-Y. Wang, R-S. Jiang, J. Li and M. Shi, Eur. J. Org. Chem., 4002 (2005)
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  • This compound has been previously reported, but no procedure or spectral data were given, see , Wilt , J. W. and Pawlikowski , W. W. Jr. 1975 . J. Org. Chem. , 40 : 3641 M. Clackers, D. M. Coe, D. A. Demaine, G.W. Hardy, D. Humphreys, G. G. A. Inglis,M. J. Johnston, et al., Bioorg. Med. Chem. Lett., 17, 4737 (2007).
  • This compound was prepared as generally described in and Maercker , A. 1965 . Org. React. , 14 : 270 L. F. Fieser and M. Fieser, Reagents for Organic Synthesis, 1, 112 (1967).
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