Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Ritter Reactions. V. Further Investigation of the 3-Azatricyclo[5.3.1.04,9]undec-2-ene System

ICC Bong, AT Ung, DC Craig, ML Scudder and R Bishop

Australian Journal of Chemistry 42(11) 1929 - 1937
Published: 1989

Abstract

2,6-Dimethylenebicyclo[3.3.1] nonane (1) and acetonitrile react under Ritter reaction conditions to produce exo-ll-acetamido-2,4,endo-ll-trimethyl-3-azatricyclo[5.3.1.04,9 ]undec-2-ene (2)monohydrate whose crystal structure [C15H24N2O.H2O, P 21, a 8.21 3(3), b lO.84l(l),c 8.234(2) Å, β 95. 57(2)º, Z 2] was determined with a final R 0.036. The diene (1) reacts similarly with benzonitrile to produce the phenyl-substituted analogue (3). In contrast, the reaction of (1) and benzyl cyanide yields a different type of product, 2-benzoyl-4,endo11-dimethyl-exo-11-phenylacetamido-3-azatricyco[5.3.1.04,9]undec-2-ene (5a), where one of the two nitrile -derived groups has undergone spontaneous oxidation during the one-flask preparation. p- Bromo - and p- chloro-benzyl cyanides behave in a similar manner yielding the adducts (5b,c) respectively.

https://doi.org/10.1071/CH9891929

© CSIRO 1989

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions