
%0 Journal Article
%A Ridley, DD 
%A Simpson, GW 
%T Preparations of 3-substituted Tetra- and Hexa-hydroazocin-2(1H)-ones and derivatives
%J Australian Journal of Chemistry
%D 1981/03/01
%V 34
%N 3
%P 569-581
%K 
%R https://doi.org/10.1071/CH9810569
%U https://www.publish.csiro.au/paper/CH9810569 
%X 3-Bromo- and 3-chloro-hexahydroazocin-2(1H)-one undergo dehydrohalogenation rather than substitution reactions, even in the presence of weakly basic nucleophiles like iodide and cyanide ions. A mixture of two alkenes is formed, with the conjugated isomer, 5,6,7,8-tetrahydroazocin-2(1H)-one, predominating over the deconjugated isomer. Only thiolate nucleophiles, for example sodium benzenethiolate, gave substitution reactions and the resulting 3-phenylthiohexahydroazocin-2(1H)- one was oxidized to give a mixture of diastereoisomeric sulfoxides. On attempted Pummerer rearrangement, this mixture of sulfoxides afforded 3-phenylthio-5,6,7,8-tetrahydroazocin-2(lH)-one rather than the expected &#945;-acyloxy sulfide. 
