TY - JOUR
T1 - Nucleophilic addition to 1,2,2,6,6-pentamethyl-3,5-dimethylene-4-piperidone
AU - Belostotskii, A. M.
AU - Shapiro, A. B.
PY - 1987/6
Y1 - 1987/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=34250097734&partnerID=8YFLogxK
U2 - 10.1007/bf00486915
DO - 10.1007/bf00486915
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SN - 0009-3122
VL - 23
SP - 665
EP - 669
JO - Chemistry of Heterocyclic Compounds
JF - Chemistry of Heterocyclic Compounds
IS - 6
ER -