The Reaction of Benzylmagnesium Chloride with Aliphatic Aldehydes¹

A versatile method for the N, N-dialkylation of aromatic amines via Grignard reactions on N,N-bis(benzotriazolylmethyl)arylamines

“…Thus, reaction of 4-(benzotriazolylmethyl)aminopyridine with benzylmagnesium chloride afforded, apart from the expected 4-phenethylaminopyridine (70%), another product, 4-(2-methylbenzy1amino)pyridine (17%). Although the fact that benzyl Grignard reagents can also undergo reactions with electrophiles as their mesomeric forms, with the negative charge localized on ent alkyl groups by stepwise Grignard reactions on 1, such the ortho carbon, is well known (35,36), such a reaction course dialkylation of arylamines succeeds well on applying a stepwise was never observed in any of our other cases where benzyl procedure. Mono-benzotriazolylmethylation of an arylamine Grignard reagent was used.…”

Ring-Opening Reactions of α,β-Epoxy Silanes with Organocopper Reagents: Reaction at Carbon or Silicon?

“…( Z )-1-(Trimethylsilyl)-1,2-epoxyoctane ( 13 ) 2b, was prepared from vinylsilane 12 by treatment with m -CPBA. 1-Phenyl-2-octanol ( 10 ) was prepared from heptanal by treatment with benzylmagnesium chloride and from 1,2-epoxyoctane by treatment with PhLi/CuCN (2:1).…”

“…(1-Octynyl)trimethylsilane (11) 33 and (1-octynyl)phenyldimethylsilane ( 14) 34 were prepared from 1-octyne by treatment with methyllithium followed by trimethylchlorosilane and phenyldimethylchlorosilane, respectively. (Z)-(1-Octenyl)trimethylsilane ( 12) 33,35 and (Z)-(1octenyl)phenyldimethylsilane ( 15) 36 10) 38 was prepared from heptanal by treatment with benzylmagnesium chloride and from 1,2-epoxyoctane by treatment with PhLi/CuCN (2:1).…”