Addition of phenyl‐, alkyl‐, alkenyl‐ and alkinyl‐ Grignard reagents to pyridine‐N‐oxide in THF leads to 5‐substituted (2 Z , 4 E )‐pentadien‐aldoximes 6 having ( E ) ( syn )‐configuration of the C, N‐double bond. The unsaturated oximes are shown to arise through an electrocyclic ring opening reaction from the primary Grignard adducts 5 . These can be trapped by protonation at low temperature.
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Schiess et al. (1974) studied this question.
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