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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 2
BKCSDE 20(2)
February 20, 1999 

Photocycloaddition of Cyclohexa-1,3-diene to Methyl Naphthoates
Taehee Noh, Sukjin Kang, Hyun Yu, Sangick Lee
The photocycloaddition reactions of cyclohexa-1,3-diene to methyl naphthoates were studied at low temperature in order to prevent facile thermal reactions during irradiation. By product analyses and low-temperature 1H NMR studies of the irradiated mixtures, the primary products were found to be the corresponding exo-[4+4] adducts fused at the 1,4-position of the naphthalene skeleton and the syn-[2+2] adducts fused at the 1,2-position. In the irradiation of methyl 1-naphthoate and cyclohexa-1,3-diene, the endo-[4+2] adduct was also isolated. The lowtemperature IH NMR studies indicated that the syn-[2+2] adduct was the major primary product in the case of methyl 1-naphthoate, and the syn-[2+2] and exo-[4+4] adducts in the case of methyl 2-naphthoate. The results were compared with those in the photocycloaddition reactions to naphthalenecarbonitriles. The regiochemistry and stereochemistry of the primary products were explained by the LUMO-LUMO interaction between the substrates.
168 - 172
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