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Published on: February 7, 2019
4,5-dehydro- and 4,5,15,16-bis(dehydro)octafluoro[2.2]paracyclophanes: facile generation and extraordinary
Merle A Battiste1, Jian-Xin Duan, Yi-An Zhai
1Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200, USA.
Abstract:
Dehydroiodination of 4-iodo- and 4,15-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]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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