Acidified alcohols as agents to introduce and exchange alkoxyls on the periphery of helicenes

Journal of Organic Chemistry

Volumn 65, Issue 3, 2000, Pages 806-814

  Dreher, Spencer D ^a   Paruch, Kamil ^a   Katz, Thomas J ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; PHENOL DERIVATIVE; QUINONE DERIVATIVE;

ACIDIFICATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS;

EID: 0033962404     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9914972     Document Type: Article

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26. The reaction was extended to the conversion of resorcinol to its monomethyl ether by: (a) Wallach, O.; Wüsten, M. Chem. Ber. 1883, 16, 149. It was extended to the conversion of phloroglucinol to its diethyl and dimethyl ethers by: (b) Will, W.; Albrecht, K. Chem. Ber. 1884, 17, 2098. (c) Will, W. Chem. Ber. 1888, 21, 602. The former extension was developed further by: (d) Merz, V.; Strasser, H. J. Prakt. Chem. 1900, 61, 103. The latter extension was developed further by: (e) Weidel, H.; Pollak, J. Monatsh. Chem. 1900, 21, 15, and references therein.
27. The reaction was extended to the conversion of resorcinol to its monomethyl ether by: (a) Wallach, O.; Wüsten, M. Chem. Ber. 1883, 16, 149. It was extended to the conversion of phloroglucinol to its diethyl and dimethyl ethers by: (b) Will, W.; Albrecht, K. Chem. Ber. 1884, 17, 2098. (c) Will, W. Chem. Ber. 1888, 21, 602. The former extension was developed further by: (d) Merz, V.; Strasser, H. J. Prakt. Chem. 1900, 61, 103. The latter extension was developed further by: (e) Weidel, H.; Pollak, J. Monatsh. Chem. 1900, 21, 15, and references therein.
28. The reaction was extended to the conversion of resorcinol to its monomethyl ether by: (a) Wallach, O.; Wüsten, M. Chem. Ber. 1883, 16, 149. It was extended to the conversion of phloroglucinol to its diethyl and dimethyl ethers by: (b) Will, W.; Albrecht, K. Chem. Ber. 1884, 17, 2098. (c) Will, W. Chem. Ber. 1888, 21, 602. The former extension was developed further by: (d) Merz, V.; Strasser, H. J. Prakt. Chem. 1900, 61, 103. The latter extension was developed further by: (e) Weidel, H.; Pollak, J. Monatsh. Chem. 1900, 21, 15, and references therein.
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30. For the tautomerism of phenols, see: (a) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group, Vol. 2; Zabicky, J., Ed.; Interscience: New York, 1970; pp 168-183. (b) Thomson, R. H. Quart. Rev. Chem. Soc. 1956, 10, 27. (c) Pearson, M. S.; Jensky, B. J.; Greer, F. X.; Hagstrom, J. P.; Wells, N. M. J. Org. Chem. 1978, 43, 4617.
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32. Reference 2b and references in footnote 29 therein.
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34. This replacement took place even at ambient temperatures when the reaction times were greater than 5 min.
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39. 2 = Me, which had not, imply that the transformations did not significantly change the enantiomeric purities.
40. 2 = Me, which had not, imply that the transformations did not significantly change the enantiomeric purities.
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47. See ref 12 and footnotes 22, 55, and 56 therein.
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57. 1H NMRs match those published. Muller, P.; Pautex, N. Helv. Chim. Acta 1988, 71, 1630.
58. 13C NMRs match those published. Stuhr-Hansen, N.; Henriksen, L. Synth. Commun. 1997, 27, 89.