
%0 Journal Article
%A Bong, ICC 
%A Ung, AT 
%A Craig, DC 
%A Scudder, ML 
%A Bishop, R 
%T Ritter Reactions. V. Further Investigation of the 3-Azatricyclo[5.3.1.0<sup>4,9</sup>]undec-2-ene System
%J Australian Journal of Chemistry
%D 1989/11/01
%V 42
%N 11
%P 1929-1937
%K 
%R https://doi.org/10.1071/CH9891929
%U https://www.publish.csiro.au/paper/CH9891929 
%X 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, &#946; 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. 
