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4,5-dehydro- And 4,5,15,16-bis(dehydro)octafluoro[2.2]paracyclophanes: Facile Generation and Extraordinary Diels-Alder Reactivity

4,5-dehydro- And 4,5,15,16-bis(dehydro)octafluoro[2.2]paracyclophanes: Facile Generation and Extraordinary Diels-Alder Reactivity

Merle A Battiste, Jian-Xin Duan, Yi-An Zhai, Ion Ghiviriga, Khalil A Abboud, William R Dolbier Jr

J Org Chem. 2003 Apr 18;68(8):3078-83.

PMID: 12688775

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3345297	1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane		3345-29-7	Price

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