18955-93-6

Upstream product

• 623-58-5 sodium aceto-acetate 
• 110-83-8 cyclohexene 
• 24476-16-2 1-(3'-cyclohexenyl)-2-propanone 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 108-22-5 Isopropenyl acetate 
• 822-67-3 Cyclohex-2-enol 
• 2699-13-0 3-methoxycyclohexene 
• 1521-51-3 rac-3-bromocyclohexene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 68908-13-4 bicyclo[2.2.2]oct-5-en-2-one 
• 61363-92-6 cyclohex-2-enyl 3-oxobutanoate 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 58329-99-0 cyclohex-2-enyl methyl carbonate 
• 3675-31-8 2-(cyclohex-2-enyl)acetic acid 

Downstream Products

• 103798-00-1 4-(Cyclohexen-⁽²⁾-yl)-acetessigsaeure-aethylester 
• 96206-24-5 3-(2-Methyl-allyl)-cyclohexene 
• 62597-16-4 2-cyclohex-2-enyl-4-hydroxy-3-methyl-cyclopent-2-enone 
• 100520-78-3 3-Hydroxy-6--hexandion-(2,5) 
• 1173693-63-4 1-(cyclohex-2-enyl)-2-methyl-4-phenylbutan-2-ol 

Relevant academic research and scientific papers

Ketone-directed peracid epoxidation

Ketone carbonyl groups are shown to direct the epoxidation of cyclic alkenes with higher selectivity than that displayed by esters. An 18O labelling study is used to show that a dioxirane intermediate is not involved in these reactions.

Rhenium-catalyzed α-alkylation of enol acetates with alcohols or ethers

When benzylic and allylic alcohols were treated with enol acetate in the presence of a catalytic amount of a rhenium complex, ReBr(CO)5, the carbon-carbon bond formation of the alcohols and enol acetate smoothly proceeded to give the corresponding ketones and aldehyde in moderate to good yields. For the reaction of allylic alcohols, γ,δ-unsaturated carbonyl compounds were obtained in good yields. When ethers were used instead of alcohols as the alkylated agent, two alkyl moieties on the ethers were utilized on the reaction.

Rhenium complex-catalyzed coupling reaction of enol acetates with alcohols

The reaction of enol acetates with alcohols in the presence of a catalytic amount of a rhenium complex, such as ReBr(CO)5, produced the corresponding ketones and aldehydes in moderate to good yields. It was suggested that the preparation of an ether, an intermolecular dehydrated product, was the first step of the reaction.

InI3/me3sii-catalyzed direct alkylation of enol acetates using alkyl acetates or alkyl ethers

A combined Lewis acid of InI3 and Me3SiI was used to catalyze the direct coupling reactions of enol acetates with alkyl acetates or alkyl ethers without generating metal waste. The easily-handled alkylating reagents enlarged the application area of this coupling reaction. 2011 The Chemical Society of Japan.

InCl3/Me3SiBr-catalyzed direct coupling between silyl ethers and enol acetates

A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.

Palladium(II)-catalyzed cyclization of unsaturated hydroperoxides for the synthesis of 1,2-dioxanes

The cyclization of γ, δ-unsaturated tertiary hydroperoxides in the presence of a palladium(II) catalyst afforded 1,2-dioxanes resembling biologically active natural products. A variety of substrates were screened, and synthetic manipulations were accomplished to construct compounds with structural similarity to antimalarial targets.

Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate

(Chemical Equation Presented) The combination of catalytic palladium(0) and Trost ligand provides an effective catalyst for the rearrangement of allyl β-ketoesters. The mechanism of the transformation involves formation of π-allyl palladium intermediates which undergo enantioselective attack by ketone enolates. Decarboxylation of β-ketocarboxylates allows regiospecific generation of enolates under extremely mild conditions.

Rhodium-catalyzed substitution of allylic carbonates with enoxysilanes

Substitution at the allylic position proceeds smoothly in rhodium-catalyzed reactions of allyl carbonates with enoxysilanes under almost neutral conditions to give γ,δ-unsaturated ketones in good to excellent yields. (C) 2000 Elsevier Science Ltd.

Ketone-directed peracid epoxidation of cyclic alkenes

Ketone carbonyl groups are shown to direct the peracid epoxidation of cyclic alkenes with greater selectivity than that displayed by esters. An 18O labelling study is used to show that a dioxirane intermediate is not involved in these reactions.

A 1,5-DIENE SYNTHESIS VIA TITANIUM AND ALUMINIUM MEDIATED REACTIONS

(1) 1,5-Dienes are readily prepared by titanium mediated methylenation of allyl esters, Claisen rearrangement followed by a second methylene transfer reaction. (2) The same 1,5-diene may be approached in "one pot" combining an allyl acetate and 3 equivalents biscyclopentadienyl-titanium-μ-chloro-μ-methylidene-bismethyl aluminium.