AT Ung

DC Craig

ICC Bong

ML Scudder

R Bishop

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) �, β 95. 57(2)�, 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.</jats:p

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

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