DIRECTIONAL EFFECTS OF SUBSTITUENTS IN OZONOLYSIS OF NAPHTHALENES . SYNTHESIS OF O-PHTHALALDEHYDES

A number of substituted naphthalenes have been ozonized and the selectivity of ozone attack determined quantitatively by conversion to the phthalic acids. Naphthalenes with electron-withdrawing substituents give predominance of attack on the ring not containing these substituents. Triphenylphosphine reduces these ozonolyses mixtures at low temperatures and results in good yields of the isolated o-phthalaldehydes. The cyclic peroxides that can be isolated from various naphthalenes are also reduced with triphenylphosphine to the corresponding o-phthalaldehydes. © 1968, American Chemical Society. All rights reserved.