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Synthesis 2001(8): 1197-1202
DOI: 10.1055/s-2001-15068
DOI: 10.1055/s-2001-15068
PAPER
© Georg Thieme Verlag Stuttgart · New York
Site-Selective Intramolecular Photocycloaddition of 2-Alkenyl-Substituted 1-Cyanonaphthalenes Depending on Additives, Solvents, and Substituents
Further Information
Received
5 March 2001
Publication Date:
24 September 2004 (online)
Publication History
Publication Date:
24 September 2004 (online)
Abstract
Irradiation of 2,3-dimethylbut-2-enyl 1-cyano-2-naphthylmethyl ether in the presence of Eu(hfc)3 in benzene site-selectively afforded the (2π + 2π) intramolecular photocycloadduct at the 1,2-position on the naphthalene ring. On the other hand, allyl 1-cyano-2-naphthylmethyl ether in the presence of Mg(ClO4)2 in acetonitrile gave the photocycloadduct at the 3,4-position as a sole product.
Key words
photochemistry - site-selectivity - cycloadditions - intramolecular photoadditions - cycloreversion
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