The phosphazene super bases BTPP 5, P-2-tBu 6, and P-4-tBu 7 mediate the rearrangement of unactivated N-alkyl-O-benzoyl hydroxamicacid derivatives 8, 11a–f, 13 and 16 to give 2-benzoyloxy amides 9, 12a–f, 14 and 17. The rate of reaction was found to be dependant upon the steric nature of the N-alkyl substituent.
Supported <i>p</i>-Toluenesulfonic Acid as a Highly Robust and Eco-Friendly Isocyanide Scavenger
作者:Jhonny Azuaje、Alberto Coelho、Abdelaziz El Maatougui、José Manuel Blanco、Eddy Sotelo
DOI:10.1021/co100035z
日期:2011.1.10
We document here the use of polymer-supported p-toluenesulfonic acid as a highly effective, robust, economical and eco-friendly isocyanide scavenger. The herein described strategy; circumvent the intense and repulsive odor of volatile isocyanides, enabling simplified and odorless workup and purifications. The usefulness of the new scavengers has been validated in a set of diverse isocyanide-based organic transformations and this approach is also amenable to parallel synthesis techniques.