The Journal of Organic Chemistry

2, 4-Dihydroxyphenanthrenes and derived ethers. Regioselective etherification of acetates

HE Zaugg, DA Dunnigan

Index: Zaugg,H.E.; Dunnigan,D.A. Journal of Organic Chemistry, 1976 , vol. 41, # 21 p. 3415 - 3419

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Abstract

Etherification of the two phenanthrene diacetates 3 and 11 using a large alkyl halide in the presence of anhydrous KzC09 in refluxing dry acetone is much more regioselective at the 2 position than is the direct alkylation of the monosodium salts of the corresponding phenanthrenediols 2 and 10. However, this regioselectivity unaccountably disappears when methyl iodide is used as the alkylating agent. Also, when the steric hindrance provided by ...