13670-83-2

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 41294-51-3 (C₄H₉)3SnO(C₆H₈CH₃) 
• 591-51-5 phenyllithium 

Downstream Products

• 90112-65-5 2-hydroxymethyl-6-methyl-cyclohexanone 
• 72009-04-2 2-Methyl-6-(2-chloro-2-propenyl)cyclohexanone 
• 86941-23-3 2-((Z)-3,7-Dimethyl-octa-2,6-dienyl)-6-methyl-cyclohexanone 
• 53206-66-9 2-Methyl-2-(3-methyl-2-butenyl)cyclohexanon 
• 78461-63-9 6-Methyl-2-(3-methyl-2-butenyl)cyclohexanone 
• 105518-31-8 2-[1-Methyl-1-(3-methyl-2-oxo-cyclohexyl)-ethyl]-malononitrile 
• 105518-23-8 Cyano-(3'-methyl-2'-oxo-bicyclohexyl-1-yl)-acetic acid ethyl ester 
• 105518-22-7 Cyano-(1'-methyl-2'-oxo-bicyclohexyl-1-yl)-acetic acid ethyl ester 
• 24785-76-0 2-benzyl-6-methylcyclohexan-1-one 
• 1206-21-9 2-benzyl-2-methyl-cyclohexanone 
• 105518-21-6 2-Cyano-3-methyl-3-(3-methyl-2-oxo-cyclohexyl)-butyric acid ethyl ester 
• 75222-38-7 trans-2-vinyl-6-methylcyclohexanone 
• 75222-38-7 cis-2-vinyl-6-methylcyclohexanone 
• 110222-94-1 C₅H₅Fe(CO)2CH₂CH(OC₂H₅)C₆H₈OCH₃ 

Relevant academic research and scientific papers

Ketone Enolization by Lithium Hexamethyldisilazide: Structural and Rate Studies of the Accelerating Effects of Trialkylamines

Mechanistic studies of the enolization of 2-methylcyclohexanone mediated by lithium hexamethyldisilazide (LiHMDS; TMS2NLi) in toluene and toluene/amine mixtures are described. NMR spectroscopic studies of LiHMDS/ ketone mixtures in toluene reve

Lithium Hexamethyldisilazide-Mediated Ketone Enolization: The Influence of Hindered Dialkyl Ethers and Isostructural Dialkylamines on Reaction Rates and Mechanisms

Mechanistic studies of the enolization of 2-methylcyclohexanone mediated by lithium hexamethyldisilazide (LiHMDS; TMS2NLi) solvated by hindered dialkyl ethers (ROR′) are described. Rate studies using in situ IR spectroscopy show that enolizatio

Reaction of Ketones with Lithium Hexamethyldisilazide: Competitive Enolizations and 1,2-Additions

Reaction of 2-methylcyclohexanone with lithium hexamethyldisilazide (LiHMDS, TMS2NLi) displays highly solvent-dependent chemoselectivity. LiHMDS in THF/toluene effect enolization. Rate studies using in situ IR spectroscopy are consistent with a THF concentration-dependent monomer-based pathway. LiHMDS in pyrrolidine/toluene affords exclusively 1,2-addition of the pyrrolidine fragment to form an α-amino alkoxide-LiHMDS mixed dimer shown to be a pair of conformers by using 6Li, 15N, and 13C NMR spectroscopies. Rate studies are consistent with a monomer-based transition structure [(TMS2NLi) (ketone)-(pyrrolidine)3]. The partitioning between enolization and 1,2-addition is kinetically controlled.

Lithium hexamethyldisilazide/triethylamine-mediated ketone enolization: Remarkable rate accelerations stemming from a dimer-based mechanism

Mechanistic studies of the enolization of 2-methylcyclohexanone mediated by lithium hexamethyldisilazide (LiHMDS; TMS2NLi) in toluene and toluene/triethylamine (Et3N) mixtures are described. Structural studies of LiHMDS/ketone mixtur

Highly Regioselective Monoalkylation of Ketones via Manganese Enolates. Prepared from Lithium Enolates

Li-enolates are readily converted to Mn-enolates by treatment with manganese halides.In THF, the reaction is easily and economically performed with manganese chloride at room temperature.Mn-enolates can then be regioselectively monoalkylated in good yields.The formation of di and polyalkylated products is never observed (1percent).

On the Structure and Reactivity of Lithium Diisopropylamide (LDA) in Hydrcarbon Solutions. Formation of Unsolvated Ketone, Ester, and Carboxamide Enolates

Enolizations of ketones, tert-butyl esters, and carboxamides by solvent-free lithium diisopropylamide (LDA) in hexane or toluene are described.Enolates are isolated as spectroscopically pure, white (often crystalline) solids.Solubilities of the enolates in hexane range from highly soluble to completely insoluble.Enolization of aldehydes, methyl esters, and acetone afford complex mixtures.Analysis of LDA and LDA in hexane by 6Li and 15N NMR spectroscopy show evidence of an equilibrium mixture of at least three cyclic oligomers.

Preparation of 1,3-Diketones and of Nitro-diketones by (1:1)-Acylation of Lithium Enolates with Acyl Chlorides

Slow addition of precooled solutions of lithium enolates in THF to solutions of equimolar amounts of acyl chlorides in the same solvent at temperatures between -80 and -100 deg furnishes 1,3-diketones in acceptable to good yields.Even 3-nitropropionyl and 4-nitrobutyryl chloride can be employed for the (1:1)-acylation of enolates to give the synthetically useful 5- and 6-nitro-1,3-diketones 13 and 25, respectively.The scope and the limitations of this method of preparing 1,3-diketones are given and are compared with alternative methods.