4,5-dehydro- and 4,5,15,16-bis(dehydro)octafluoro[2.2]paracyclophanes: facile generation and extraordinary Diels-Alder reactivity |
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Authors: | Battiste Merle A Duan Jian-Xin Zhai Yi-An Ghiviriga Ion Abboud Khalil A Dolbier William R |
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Institution: | Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200, USA. |
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Abstract: | Dehydroiodination of 4-iodo- and 4,15-diiodo-1,1,2,2,9,9,10,10-octafluoro2.2]paracyclophane by treatment with KO(t)Bu in the presence of benzene, naphthalene, anthracene, and 2.2]paracyclophane affords each of the corresponding Diels-Alder mono- and bis-cycloadducts derived from the presumed aryne intermediates in high yield. Monoadducts of t-butylbenzene and furan are also obtained in excellent yield. All of the products were characterized by their NMR spectra, with four of them also being confirmed by X-ray crystallography. The extraordinary selectivity/reactivity of the aryne intermediate is discussed. |
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