NUCLEOPHILIC ADDITION TO 1,2,2,6,6-PENTAMETHYL-3,5-DIMETHYLENE-4-PIPERIDONE

Article abstract of DOI:10.1007/BF00486915

Like branched primary amines, unbranched mercaptans react with 1,2,2,6,6-pentamethyl-3,5-dimethylene-4-piperidone to give products of ring opening.On the basis of the data obtained, a reaction scheme that includes the intermediate formation of 3,7-diazabicyclo<3.3.1>nonan-9-one seems less likely as compared with a scheme involving elimination from the monocyclic piperidine system.It is also shown that steric interaction of the vicinal substituents is one of the important factors that promote β elimination.