73195-54-7Relevant articles and documents
Stereochemistry of Aliphatic Carbocations, 13. Protonated Cyclopropanes as Intermediates in 1,2-Alkyl Shifts
Kirmse, Wolfgang,Loosen, Karin,Prolingheuer, Ernst-Christoph
, p. 129 - 141 (2007/10/02)
The nitrous acid deamination of 2-ethyl-1-methylbutylamine (10), 1,2-diethylbutylamine (35), and 2-ethyl-1-methylpentylamine (43) has been studied with respect to 1,2-alkyl shifts.Optically active and deuterated amines were employed whenever possible.The structure, configuration, and deuterium distribution of various products (e. g. 16 from 10, 40 and 48 from 35, 56 from 43) are most reasonably explained in terms of alkyl-bridged intermediates (corner-protonated cyclopropanes) which isomerize via proton shifts from corner to corner.The alternative interconversion of open ions via 1,3-H shifts is incompatible with our experimental results.