ChemInform Abstract: Ritter Reaction of Isoborneol with Monochloroacetonitrile.

Abstract

ChemInform Abstract Treatment of the readily available isoborneol (I) with conc. H2SO4 generates a non-classical cation, whose Wagner-Meerwein rearrangement takes an unexpected (bornane → isocamphane) direction to yield the desired isocamphane derivative (III) as the main product accompanied by a minor amount of the bornane derivative (IV). The derivative (III) is known as a ganglion blocker (yields are given in g).