Kinetic Stabilisation of Reactive Intermediates

Abstract: Reactive Intermediates are fundamental species in organic chemistry which are invoked to explain the course and outcome of many and most chemical reactions. The value of stabilizing such intermediates so that they can be directly studied has been recognized for many years. The fundamental information so obtained further enhances our understanding and therefore augments our ability to predict the outcome of chemical reactions. Accordingly, building on our recent work1 using the adamantyl grouping so to obtain the first stable bromoallene oxide (and the first crystalline allene oxide of any kind), we will adopt this strategy to target the first stable (and designed to be crystalline) acyclic bromonium ions [RBrR]+ X-. This strategy will also be employed to target the first stable 2-alkyl 1,3-dioxolan-2-ylium ions, as well as stable quinone methides.

1. Braddock, D. C.; Mahtey, A.; Rzepa, H. S.; White, A. J. P. Chem. Commun. 2016, 52, 11219 - 11222.