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A novel thermal epoxidation of a bicyclo[3.1.0]hex-2-ene by molecular oxygen

✍ Scribed by Albert Padwa; Lee Brodsky

Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
197 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis

AS an extension of our studies on the photochemical Diels-Alder reaction of 1,3,5-hexatrienes to bicyclo[3.l.O]hex-2-enes, 1 we became interested in determining the stereochemical consequences attending the thermal cycloreversion of the bicyclo[3.l.O]hex-2-ene system. The parent carbocycle is known to display interesting thermal chemistry.

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✍ Behrendt, Uwe ;Gabor, Barbara ;Mynott, Richard ;ButenschΓΆn, Holger πŸ“‚ Article πŸ“… 2006 πŸ› John Wiley and Sons 🌐 English βš– 996 KB

## Abstract The chemistry of the highly substituted cyclobutanone derivative 2, which is easily accessible from 1, is dominated by the steric hindrance caused by the substitutents: Reduction with hydride reagents and nucleophilic additions with methyllithium are less stereoselective than correspond