5384-59-8Relevant academic research and scientific papers
Tertiary alcohols by tandem β-carbolithiation and N→C aryl migration in enol carbamates
Fournier, Anne M.,Clayden, Jonathan
, p. 142 - 145 (2012/02/14)
Enol carbamates (O-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and bearing an N-aryl substituent undergo carbolithiation by nucleophilic attack at the (nominally nucleophilic) β position of the enol double bond. The resulting carbamate-stabilized allylic, propargylic, or benzylic organolithium rearranges with N→C migration of the N-aryl substituent, creating a quaternary carbon α to O. The products may be readily hydrolyzed to yield multiply branched tertiary alcohols in a one-pot tandem reaction, effectively a polarity-reversed nucleophilic β-alkylation-electrophilic α-arylation of an enol equivalent.
ONE-STEP SYNTHESIS OF KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS IN THE PRESENCE OF A NICKEL(II)-PHOSPHINE CATALYST.
Fiandanese, V.,Marchese, G.,Ronzini, L.
, p. 3677 - 3680 (2007/10/02)
A one-step synthesis of diaryl and alkyl-aryl ketones by the reaction of carboxylic acid with Grignard reagents in the presence of NiCl2(Ph2PCH2CH2PPh2) as catalyst is described.In the nickel-catalyzed Grignard reaction the formation of alcohols is nearly completely suppressed.
