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The solvolysis of 5-keto-2-norbornyl brosylates

โœ Scribed by Joe C. Greever; Donald E. Gwynn

Book ID
104239144
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
195 KB
Volume
10
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Numerous studies have shown the P-norbornyl cation to exhibit a remarkable degree of exo-stereospecificity upon nucleophilic substitution. 1 2-4 Some recent work, however, has shown this stereospecificity to be lost upon incorporation of an electron withdrawing substituent located either 01 or S to the developing cationic center. We wish to report a similar observation in the solvolysis study of 5-keto-exo-and endo-2-norbornyl brosylates* (I and II, respectively), a system in which a deactivating carbonyl group is situated three carbons distant from the site of ionization.

๐Ÿ“œ SIMILAR VOLUMES

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a, B and Y deuteriw isotope effects have been used extensively to probe the nature of the norbornyl cation3(a)-3(i) generated solvolytically. Of special interest has been the work of Uurr et al. 3(c) and Bo&ii( et a1.3(d) which showed that the isotope