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Endocyclic vs exocyclic olefin formation from 4‐piperidones via the wittig reaction
Author(s) -
Borne Ronald F.,
AboulEnein Hassan Y.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090419
Subject(s) - chemistry , wittig reaction , sodium borohydride , olefin fiber , double bond , medicinal chemistry , base (topology) , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics
The reaction of 1‐methyl‐4‐piperidone and 1‐benzoyl‐4‐piperidone with triethyl phosphono‐acetate in the presence of excess base yields both the endocyclic and exocyclic olefins. However, treatment of 1‐methyl‐4‐piperidone with diethyl cyanomethylphosphonate, even in the presence of excess base, yielded only the exocyclic olefin. Factors affecting isomer distribution during the course of the reaction are presented. The isolation of an exocyclic tetrahydropyridine from the sodium borohydride reduction of the methiodide of 4‐pyridylacetonitrile is reported.