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Synthesis and acetolysis of the epimeric 7-tosyloxynorbornan-2-ones

✍ Scribed by Gassman, Paul G.; Marshall, James L.; Hornback, Joseph M.

Book ID
126086982
Publisher
American Chemical Society
Year
1969
Tongue
English
Weight
926 KB
Volume
91
Category
Article
ISSN
0002-7863

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Acetolysis of the epimeric 3,3-dimethyl-
Acetolysis of the epimeric 3,3-dimethyl-7-tosyloxybicyclo[2.2.1]Heptan-2-ones
✍ Paul G. Gassman; Joseph M. Hornback πŸ“‚ Article πŸ“… 1969 πŸ› Elsevier Science 🌐 French βš– 200 KB

Recently we reported that the rate determining step in the unusually rapid solvolysis of anti-7-tosyloxybicyclo[2.2.l]heptan-2-one (I.) was the conversion of 1 into its enol, & The enol then ionized in a fast step to give an intermediate which collapsed to give 2 with complete retention of stereoche