Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction

A Hassner, R Maurya, O Friedman…

Index: Hassner, Alfred; Maurya, Rakesh; Friedman, Oded; Gottlieb, Hugo E.; Padwa, Albert; Austin, David Journal of Organic Chemistry, 1993 , vol. 58, # 17 p. 4539 - 4546

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Citation Number: 67

Abstract

Thermal intramolecular oxime olefin cycloaddition of a-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo [3.3. 0] octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one ...