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Grignard‐Addition an Pyridin‐N‐oxid
Author(s) -
Schiess Peter,
Monnier Charles,
Ringele Peter,
Sendi Ebrahim
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570620
Subject(s) - chemistry , protonation , pyridine , medicinal chemistry , ring (chemistry) , reagent , adduct , alkyl , double bond , grignard reagent , grignard reaction , organic chemistry , ion
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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