68698-26-0Relevant academic research and scientific papers
Stereochemistry of Aliphatic Carbocations, 14. Alkyl Shifts from Secondary to Primary Carbon Atoms
Kirmse, Wolfgang,Guenther, Bernd-Rainer,Knist, Johannes,Kratz, Sigrid,Loosen, Karin,et al.
, p. 2127 - 2139 (2007/10/02)
Alkyl shifts from secondary to primary carbon atoms have been induced by the nitrous acid deamination of suitable amines (4, 22, 39, 51); they include sequential rearrangements (-CH3,CH3 and -CH3,H).Predominant although incomplete inversion at the migration origin has been observed (Me 70percent, Et 62-64percent, nPr 65percent, iPr 64percent, tBu 55percent).Our results require the intervention of open secondary carbocations which may be preceded by less stable bridged intermediates.
