Dittami, James P.
Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. Previous work has shown that photolysis of aryl vinyl ethers 26 and 29 gives carbonyl ylide intermediates which undergo subsequent intramolecular ylide-alkene addition reactions. The photoinitiated-intramolecular addition reaction of aryl vinyl ether 18, which incorporates a pendant alkene side chain was proposed as an approach to the synthesis of the acetylcholineterase inhibitor huperzine A. Studies of this synthetic route lead to an interesting photoproduct produced by the irradiation of aryl vinyl ether 48 in methanol. It is believed that this product is the result of an -cleavage of 50 followed by internal disproportion to produce ketene 61 which is trapped by methanol to produce 52.
Worcester Polytechnic Institute
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Chemistry and Biochemistry