134126-24-2Relevant articles and documents
Mechanism of the Grignard Addition Reaction. XV. The Reaction of Grignard Reagents with Benzylpyridinium Chloride
Holm, Torkil
, p. 276 - 279 (2007/10/02)
The reaction of Grignard reagents with benzylpyridinium chloride produces 2-alkyl-N-benzyl-1,2- and 4-alkyl-N-benzyl-1,4-dihydropyridines.The mechanism seems to be polar, concerted except for the t-butylmagnesium reagent.The adducts may reduce the starting material to the unreported, non-alkylated N-benzyl-1,4-dihydropyridine.If the Grignard-alkyl is secondary, crystalline 4-alkylidene-1,4-dihydropyridines may be produced.Thermal rearrangements of N-benzyl-1,4-dihydropyridines lead to migration of the benzyl group.