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Cycloaddition Reactions of 1,4‐Dihydronaphthalene‐1,4‐epoxide with Cyclohexadiene and 7‐(Methoxycarbonyl)cycloheptatriene: Selectivity in Additions
Author(s) -
Menzek Abdullah,
Altundaş Aliye,
Çoruh Ufuk,
Akbulut Nihat,
López Ezequiel M. Vázquez,
Hökelek Tuncer,
Erdönmez Ahmet
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300569
Subject(s) - cycloaddition , cycloheptatriene , chemistry , selectivity , epoxide , naphthalene , medicinal chemistry , adduct , halogenation , organic chemistry , catalysis
Cycloaddition reactions of naphthalene‐1,4‐epoxide ( 1 ) with both 7‐(methoxycarbonyl)cycloheptatriene ( 2 ) and cyclohexadiene ( 4 ) give adducts of type 3 and 5 exclusively. Selectivity was observed for the cycloaddition and bromination reactions, but neighboring group participation also occurrs in the latter. The formation of the products is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)