Electrophile initiated acetylenic oxy Cope rearraqemmt of divmelysubstituted 5-Hcxen-1-yn-3-01s leads to the cwrespuWgaC6 -diethylmlc aldehydes or ketones In 9ood yields wlth mainly the E conf iguraticn fw both tile bonds. Silver nitrate and Silver triflwromethanesulfonate appear to be the most suit
The aromatic oxy-Cope rearrangement
โ Scribed by Ellio N Marvell; Stephen W Almond
- Book ID
- 104237839
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 107 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
An aromatic oxy-Cope rearrangement can be achieved under anionic conditions (KH f HMPAl in
Zow yield with a nuphthalene ring but not a phenyt.
We have recently measured the activation parameters for an aromatic Cope rearrangement,l and these sug,oest that rearrangement of 4-phenyl-1-butene would require AH # = 42 kcal/mol.
Searching for ways to reduce this barrier, we were quite obviously attracted by the large reduction in activation energy associated with the anionic oxy-Cope rearrangement.2 Thus, we initiated a study of the aromatic oxy-Cope rearrangement, and we are now prompted to report our
๐ SIMILAR VOLUMES
## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
The reversibility of the thermal oxy-Cope rearrangement is demonstrated with the specific example 10 t 11, and the pathway and energetics associated with this phenomenon are outlined.