A consideration of earlier results suggests that in contrast to other simple 1 -alkylnaphthalenes, the barrier to rotation of the neopentyl group in 1 -neopentylnaphthalene may be high enough to be measured by dynamic n.m.r. spectroscopy. A synthesis is reported, and changes in the n.m.r. spectrum at low temperature suggest a barrier to rotation of 5.1 5 kcal mol-l. Molecular mechanics calculations and difference NOE n.m.r. experiments suggest the structure of the ground state and transition state conformations, and the latter is not, apparently, the one with the t-butyl group in the plane of the naphthalene ring. The barrier to rotation of the naphthyl group in the much more highly substituted 2-tbutyl-2-(1 -naphthyl)-l,3-dioxolane is only 5.1 5 kcal mol-' as shown by two methyls of the slowly rotating t-butyl group becoming diastereotopic as rotation of the naphthyl group also becomes slow.
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