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

Dehydroiodination of 4-iodo- and 4,15-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane by treatment with KOtBu 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 i...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2003-04, Vol.68 (8), p.3078-3083
Main Authors: Battiste, Merle A, Duan, Jian-Xin, Zhai, Yi-An, Ghiviriga, Ion, Abboud, Khalil A, Dolbier, William R
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Dehydroiodination of 4-iodo- and 4,15-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane by treatment with KOtBu 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0268815