NUCLEOPHILIC ADDITION OF NITRILES TO TERTIARY MONOCYCLIC TERPENES ALCOHOLS

Article abstract of DOI:10.1007/BF00598756

Previously unknown secondary amines have been synthesized by the Ritter reaction of p-menthan-8-ol with propio- and benzonitriles.The performance of this reaction with α-terpeneol and benzonitrile led to the formation of a mixxture of N-(p-menth-1-en-8-y1)benzamide and N, N-(p-menth-1,8,diyl)dibenzamide.A transdiamide was also obtained on the reaction of α-terpineol with isovaleronitrile.The use of propionitrile as the nucleophile with α-terpineol led to the formation of 2-ethyl-4,4,8-trimethyl-8-propionamido-3-azabicyclo <3.3.1>non-2-ene.