Straining strained molecules. II. The syntheses and spectral properties of some ace-bridged naphthalenes

Abstract

Reaction of both peri-dilithionaphthalene and peri-dilithioacenaphthalene with acenaphthenequinone and pyracenequinone yielded the dihydroxy derivatives of acenaphth[1,2-a]-acenaphthylene 11a, 11b, 11c with no, one, and two ace-bridges respectively. These could be converted either by the Corey thionocarbonate method or with anhydrous liquid hydrogen fluoride to the three alkenes 12a,b,c and with Pb(OAc)4 to the three diketones 13a,b,c. The latter on Wolff–Kishner reduction yielded alkenes 12a,b and mono ketones 15b,c. The uv, ir, 1Hmr spectra and electrode reduction potentials for the four series of compounds in which the ace-bridges add increments of strain were examined and possible effects which might be due to strain were noted. Several areas in which theoretical calculations are lacking were noted.