78411-32-2Relevant academic research and scientific papers
Preparations of 3-Substituted Tetra- and Hexa-hydroazocin-2(1H)-ones and Derivatives
Ridley, Damon D.,Simpson, Gregory W.
, p. 569 - 581 (2007/10/02)
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(1H)-one rather than the expected α-acyloxy sulfide.
