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ChemInform Abstract: Stereoselectivity of Destabilized Carbocations: 1-Cyano-2-adamantyl and 3-Cyano-4-protoadamantyl Cations.

✍ Scribed by K. GOMANN; E. HERPERS; W. KIRMSE

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereoselectivity of Destabilized Carbocations: 1-Cyano-2-adamantyl and 3-Cyano-4-protoadamantyl Cations.

-Heating of the derivative (I) in dioxane/H 2 O leads to a ion pair which undergoes nearly complete and stereospecific recombination. In contrast, the 3-cyano-4-protoadamantyl cation derived from the isomer (IV) undergoes recombination, solvolysis, and elimination competitively, demonstrating that the endo selectivity of the parent 4-protoadamantyl cation is lost on introduction of 3-CN group. -(GOMANN,

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