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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 9
BKCSDE 18(9)
September 20, 1997 

 
Title
[4+4] Cyclodimer of tert-Butyl 9-Anthroate and Furan and [4+4] Cyclodimers of Alkyl 9-Anthroate
Author
Taehee Noh*, Heejun Lim, Daekyun Kim, Kyungmoon Jeon
Keywords
Abstract
Irradiation of tert-butyl 9-anthroate and furan through a Uranium glass filter gave the [4+4] cyclodimer (21.8%) of tert-butyl 9-anthroate and furan and the 1,4-10',9' cyclodimer (4.2%) of tert-butyl 9-anthroate as well as the 9,10-10',9' cyclodimer (65.7%) of tert-butyl 9-anthroate. The [4+4] cyclodimer of tert-butyl 9-anthroate and furan was found to be thermally dissociated into their unit components with the activation enthalpy of 35.6 kcal/mole and the activation entropy of 7.6 eu, and photochemically dissociated to produce excited tert-butyl 9-anthroate. Quantum yields for the photodissociation to tert-butyl 9-anthroate and the formation of excited tert-butyl 9-anthroate in cyclohexane at room temperature were determined to be 0.56 and 0.19, respectively. The 1,4-10',9' cyclodimer of tert-butyl 9-anthroate in DMF was thermally dissociated into tert-butyl 9-anthroate with the activation enthalpy of 34.8 kcal/mole and the activation entropy of 16.4 eu. Upon irradiation, the [4+4] cyclodimers of tert-butyl 9-anthroate and the [4+4] cyclodimers of methyl 9-anthroate were quantitatively dissociated. However, no adiabatic photoreversion was observed from any of the cyclodimers. Quantum yields for the photodissociation in cyclohexane at room temperature were measured and compared.
Page
998 - 1002
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