32207-07-1

Upstream product

• 58193-39-8 8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 
• 78-79-5 isoprene 
• 124816-38-2 β-atlantone 
• 4786-24-7 3,3-dimethylacrylonitrile 
• 60699-34-5 2-(1'-methyl-4'-cyclohexenyl)-3-bromo propene 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 6090-09-1 (+-)-4-acetyl-1-methylcyclohexene 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 5989-27-5 D-limonene 
• 121726-27-0 methyl-3 N-phenyl butene-3 imidothioate de methyle 
• 138-86-3 limonene. 

Downstream Products

• 38142-58-4 (+/-)-ar-turmerone 
• 30666-87-6 (±)-2-methyl-6-(p-tolyl)heptan-4-one 

Relevant academic research and scientific papers

One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds

TiCl4-promoted aldol reaction of ketones as aldol acceptors followed by elimination of the titanoxy group from the Ti-aldolates affords β,β-disubstituted α,β-unsaturated carbonyl compounds in a one-pot procedure. The use of additives, such as DMF, N,N,N′,N′-tetramethylethylenediamine, and pyridine, in the elimination step was found to be important.

Synthese de cetones a partir de N-phenyl imidothioesters et par l'intermediaire de cetenimines

The thermal decomposition of metallated N-phenyl imidothioesters (lithium or magnesium alkylthio-enaminates generated by either deprotonation or 1,4-addition) led to ketenimines which were trapped in situ by organo-lithium or magnesium compounds to give metallated imines, readily hydrolysed into ketones.This sequence allowed the use of imidothioesters as acyl cation equivalents and also successive and regioselective > 1,3-additions of two different organometallics to an α-unsaturated imidothioester.Ar-turmerone, 2,6-dimethyl-2,7-octadien-4-one, iso-artemisia ketone, α-atlantone and other unsymmetrical ketones were synthesized by this procedure.

CONDENSATION DES NITRILES AVEC LES ORGANOZINCIQUES ALLYLIQUES. APPLICATIONS EN SERIE TERPENIQUE

The reaction of 3-bromomethyl-2,5-dihydrothiophen-1,1-dioxide 6 and 2-bromomethyl-1,3-butadiene 7 with nitriles in the presence of the zinc-silver couple leads to a mixture of ketones 8,9, the pyrolysis of which give the ketones 10 and 11, corresponding respectively to acylation of isoprene at its methyl group from 8, and at C-3 from 9.The reaction of bromide 7 with nitriles leads also to the formation of ketones 10 which by acid isomerisation give the ketones 12 corresponding to an acylation at C-1 of isoprene.In the same way the reaction of 2-(1'-methyl-4'-cyclohexenyl)-3-bromo propene 13 with 3,3-dimethyl acrylonitrile give β- atlantone 14 which is isomerised in acidic medium to α-atlantone 15. 10,11-dihydro α and β-atlantone 16, 17 are obtained by the same procedure from 13 and 3-methyl butyronitrile.