84790-10-3Relevant academic research and scientific papers
Evidence for 4-Homocubyl Carbenium Ions as Reactive Intermediates
Mergelsberg, Ingrid,Langhals, Heinz,Ruechardt, Christoph
, p. 360 - 366 (2007/10/02)
4-(Hexafluoroisopropoxy)homocubane (6) is the main product of the thermolysis reaction of N-(4-homocubyl)-N-nitrosoacetamide (9) and of the solvolysis reaction of 4-homocubyl bromide (5) in hexafluoro-2-propanol.This is experimental evidence for 4-homocubyl carbenium ions as intermediates in both reactions.The solvolysis rate of 4-homocubyl bromide at 120 deg C in the same solvent (k1120deg C = 1.3 * 10-7 s-1) by far exceeds that of 1-norbornyl bromide which does not react at a detectable rate under these conditions.According to force field calculations the strain enthalpy is increasing by as much as 66 kcal * mol-1 in the ionisation of 4-homocubyl bromide.Therefore nonclassical stabilization of the 4-homocubyl carbenium ion is postulated.
