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Deamination Reactions, 56. Cyclopropane Participation in Norbornyl Cations

✍ Scribed by Herrmann, Roland ;Kirmse, Wolfgang

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
306 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Norbornanediazonium ions / endo Selectivity / Norpinyl cations / Cyclopropylcarbinyl cations Nitrous acid deamination of spiro[bicyclo[2.2.l]heptane-7,1'cyclopropan]-endo-2-amine (13) affords 74% of the analogous endo alcohol 24-OH and 26% of the rearranged exo alcohol 25-OH. The exceptional preference for endo attack of the nucleophile is attributed to intervention of the bridged norpinyl cation 21 which is stabilized by the spiroannellated cyclopropane ring. The spiro[bicyclo[2.2.1]heptane-3,1'-cyclopropanl-2-yl cations 23 arising from Wagner-Meerwein rearrangement are captured by water to give high exo:endo product ratios. OR 7 8

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