Experiments directed towards the synthesis of anthracyclinones. VII. Model studies with allyl naphthalenyl ethers

Abstract

The Claisen rearrangement of some allyl naphthalen-1-yl ethers has been examined, together with methods for modification of the resulting 2-ally1 side chain. Isomerization of the C-allyl substituent to a prop-1-enyl group followed by ozonolysis gives a formyl derivative, while ozonolysis of a 2-(2-methylprop-2-enyl) moiety or mercuriation of a 2-(2-chloroprop-2-enyl) substituent leads to an acetonyl derivative.

Treatment of phenols with iodine(I) acetate and an excess of silver(I) acetate gives 4-hydroxyaryl acetates, probably via dienone intermediates.