Author:
Cole ER,Crank G,Stapleton BJ
Abstract
Oxidations of 1- and
2-methoxy-, and 1,5- and 2,6-dimethoxy-naphthalene were performed thermally and
photochemically with various oxidant/reactant ratios. A wide variety of
products including acetoxy derivatives, dimers, o- and p-quinones
(monomeric, dimeric and polymeric) and polysubstituted derivatives were formed
demonstrating the high reactivity of naphthalene ethers. Higher ratios of
oxidant gave increased yields of quinones, but photochemical reactions gave
virtually the same mixtures of products as thermal processes. The position of
the methoxy group controlled the initial attack by the reagent: for 1-methoxy-
and 1,5-dimethoxy-naphthalene the 4-position is the site of reaction, while for
2-methoxy- and 2,6-dimethoxy-naphthalene position 1 reacts. Results indicate
that initial products are further oxidized to the more complex structures
found. Several different mechanistic paths are required to explain the variety
of products.
Cited by
15 articles.
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