Synthesis and Structural Characterization of Novel Camphor‐derived Amines

Abstract

Two novel 4-substituted camphidine derivatives 10a,b have been prepared from (+)-camphor (1) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b, formed as a side product during the hydrogenation of arylidene ketone 3b, under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12. (1S)-(+)-Camphorquinone (13) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17, an N-heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X-ray analysis.