1-Phenylisobenzofuran, 1-phenylnaphtho [2, 3-c] furan, 1-phenylnaphtho [1, 2-c] furan, and 3-phenylnaphtho [1, 2-c] furan via cyclic hemiaminal, hemiacetal, and …

…, IJ Munday, RE Sandborn, PW Dibble

Index: Smith, James G.; Fogg, Deryn E.; Munday, Ian J.; Sandborn, Richard E.; Dibble, Peter W. Journal of Organic Chemistry, 1988 , vol. 53, # 13 p. 2942 - 2953

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Citation Number: 26

Abstract

The title compounds have been generated via cyclic hemiaminal, hemiacetal, and acetal precursors and trapped in Diels-Alder reactions with several dienophiles. The precursors are easily prepared from o-bromobenzyl alcohol, 2-brom0-3-naphthalenemethano1, or 1- bromo-2-naphthalenemethanol. Metalation of the bromo alcohols followed by reaction with benzonitrile gave cyclic hemiaminals. In the presence of acid, the hemiaminals eliminate ...