NUCLEOPHILIC ADDITION OF NITRILES TO TERTIARY MONOCYCLIC TERPENES ALCOHOLS
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 non-2-ene.
STEREOSELECTIVE SYNTHESIS OF N,N'-DIACYL-p-MENTHANE-1,8-DIAMINES
It has been shown that the interaction of terpin hydrate with various nitriles under the conditions of the Ritter reaction takes place stereoselectively and leads to the formation of a mixture of isomeric cis- and trans-N,N'-diacyl-p-menthane-1,8-diamines in a ratio of 1:4.The structures of the products have been shown by 1H and 13C spectroscopy.
Kovals'skaya, S. S.,Kozlov, N. G.,Tikhonova, T. S.
p. 552 - 557
(2007/10/02)
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