Journal of the Chemical Society. Perkin transactions II p. 286 - 297 (1981)
Update date:2022-08-10
Topics:
Jackson, Anthony H.
Shannon, Patrick V. R.
Taylor, Paul W.
Both 4-(1-naphthyl)butanol and 4-(2-naphthyl)butanol cyclised in refluxing boron trifluoride-ether to give 1,2,3,4-tetrahydrophenanthrene.By use of the corresponding 1,1-dideuteriobutanol derivatives and analysis of the products by 220 MHz 1H n.m.r. spectroscopy it has been demonstrated that the 1-naphthylbutanol cyclises by two distinct pathways, (a) by direct attack (84percent) at the 2-position, and (b) by ipso-attack (16percent) at the 1-position of the naphthalene nucleus, followed by rearrangement.The 2-naphthylbutanol cyclises exclusively by direct substitution at the 1-position.With 4-(4-methoxy-1-naphthyl)-1,1-dideuteriobutanol on the other hand the proportion of ipso-substitution rises to 71 percent as shown by the 360 MHz 1H n.m.r. spectra of the resulting mixture of tetrahydrophenanthrenes.
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(1980)
