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4,5-Dehydrooctafluoro[2.2]paracyclophane: facile generation and extraordinary Diels–Alder reactivity

✍ Scribed by Merle A. Battiste; Jian-Xin Duan; Yi-An Zhai; Ion Ghiviriga; Khalil A. Abboud; Adrian Roitberg; G.Robert Shelton; William R. Dolbier Jr.

Book ID: 104251879
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 191 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01554-x

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✦ Synopsis

Dehydroiodination of 4-iodo-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, or t-butylbenzene affords each of the corresponding Diels-Alder cycloadducts of the presumed aryne intermediate in high yield. The products were characterized by their NMR spectra, with one of them also being confirmed by X-ray crystallography. The extraordinary selectivity/reactivity of the aryne intermediate is discussed.

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