| Abstract
| - Irradiation of phthalimides which contain N-linked ω-trimethylsilylmethyl-substituted polyether,polythioether, and polysulfonamide chains results in efficient production of the correspondingmacrocyclic polyether, polythioether, and polysulfonamide products. These photocyclization reactionsfollow sequential single electron transfer (SET)−desilylation pathways. Only in the cases ofphthalimides, bearing mixed ether-thioether N-substituents, do these excited-state cyclizationreactions proceed with lower degrees of regioselectivity. This is a result of competitive desilylationand α-to-sulfur deprotonation reactions of the zwitterionic diradical intermediates formed by initialSET.
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