Flippin, Lee A.; Muchowski, Joseph M.; Carter, David S. published the artcile< Directed metalation of aromatic aldimines with lithium 2,2,6,6-tetramethylpiperidide>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is lithiation aromatic aldimine lithium tetramethylpiperidide; piperidide lithiotetramethyl lithiation aldimine; benzaldehyde methyl.
N-Cyclohexyl aromatic aldimines are ortho-lithiated or o-methyl-lithiated with 2 equiv of lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF solution at -15°. The lithiated intermediates generally reacted with alkyl halides or CO2 to provide ortho-functionalized aldimine products which could be readily converted to the corresponding aldehydes by hydrolysis with aqueous 4 M HCl. Aromatic aldimines derived from (±)-trans-2-methylcyclohexylamine or 3-amino-2,4-dimethylpentane are resistant toward C=N addition with 1 equiv of n-BuLi at 0° in THF solution; however, they are also surprisingly resistant toward directed metalation reactions with either LTMP or n-BuLi. Exceptions to the ortho-directing and o-methyl-directing effects of the aldimine group were observed in a reaction of 3-methylthiophene-2-carboxaldehyde cyclohexylimine with LTMP, followed by CH3I, which gave a 9:1 mixture of 3,5-dimethylthiophene-2-carboxaldehyde cyclohexylimine and 5-ethyl-3-methylthiophene-2-carboxaldehyde cyclohexylimine, and a reaction of p-tolualdehyde 2,4-dimethylpent-3-ylimine with either n-BuLi or LTMP, followed by CH3I, which gave p-ethylbenzaldehyde 2,4-dimethylpent-3-ylimine.
Journal of Organic Chemistry published new progress about Aldimines Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem