
TY  - JOUR
A1  - Ridley, DD 
A1  - Simpson, GW 
T1  - Preparations of 3-substituted Tetra- and Hexa-hydroazocin-2(1H)-ones and derivatives
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1981
VL  - 34
IS  - 3
SP  - 569
EP  - 581
KW  - 
UR  - https://doi.org/10.1071/CH9810569 
N2  - 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. 
ER  -

