Abstract
A number of 9-[(arylmethoxy)methyl]anthracenes were prepared and their photoreactivity was studied. The intramolecular [4π+4π]cycloaddition competes with the intermolecular head-to-tail [4π+4π] cyclodimerization. The aryl substituents control the selectivity; concentration only plays a role in selectivity in certain cases. The complete reversibility of the cycloaddition makes this process suitable as a molecular switch, provided that traces of acids are avoided; when acid is present the cyclomers pursue an irreversible enol ether cleavage route.
Key words
cycloaddition - cyclodimerization - ether cleavage - regioselectivity - retrocycloaddition
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