135068-48-3Relevant academic research and scientific papers
Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement
Ott, Amy A.,Packard, Mary H.,Ortuno, Manuel A.,Johnson, Alayna,Suding, Victoria P.,Cramer, Christopher J.,Topczewski, Joseph J.
, p. 8214 - 8224 (2018/06/13)
The spontaneous rearrangement of allylic azides is thought to be a sigmatropic reaction. Presented herein is a detailed investigation into the rearrangement of several allylic azides. A combination of experiments including equilibrium studies, kinetic ana
Amide Acetal Claisen Rearrangement in the Synthesis of Mesembrane Alkaloids
Bauermeister, Sieglinde,Gouws, Izebrandt D.,Strauss, Heinrich F.,Venter, Elise M. M.
, p. 561 - 565 (2007/10/02)
The synthesis of primary and secondary allylic alcohols (differing in the degree of steric hindrance) and of amide acetals (achiral and chiral) is reported.These compounds were used as substrates in the amide acetal Claisen rearrangement, and the effect of Lewis acids on the stereoselectivity of the reaction was studied.The rearrangement products have been applied to the synthesis of the mesembrane alkaloids (-)-mesembranone, rac-O-methyljourbertiamine and joubertiamine.
