Cycloaddition reactions of 1,4-dihydronaphthalene-1,4-epoxide with cyclohexadiene and 7-(methoxycarbonyl)cycloheptatriene: Selectivity in additions

Menzek, A; Altundas, A; Coruh, Ufuk; Akbulut, N; Lopez, EMV; Hokelek, T; Erdonmez, A

doi:10.1002/ejoc.200300569

Cycloaddition reactions of 1,4-dihydronaphthalene-1,4-epoxide with cyclohexadiene and 7-(methoxycarbonyl)cycloheptatriene: Selectivity in additions

Menzek A., Altundas A., Coruh U., Akbulut N., Lopez E., Hokelek T., ...Daha Fazla

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, cilt.2004, sa.5, ss.1143-1148, 2004 (SCI-Expanded)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 2004 Sayı: 5
Basım Tarihi: 2004
Doi Numarası: 10.1002/ejoc.200300569
Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Index Chemicus (IC)
Sayfa Sayıları: ss.1143-1148
Anahtar Kelimeler: alcohols, bromination, cycloaddition, halogenation, HIGH-TEMPERATURE BROMINATION, 1,3-DIPOLAR CYCLO-ADDITIONS, BENZHOMOBARRELENE DERIVATIVES, REARRANGEMENT REACTIONS, CONTAINING HETEROCYCLES, DOUBLE-BOND, 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE, BEHAVIOR, ADDUCTS, SPECTRA
Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

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. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.