16538-91-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 5159, 1983 DOI: 10.1016/S0040-4039(00)88385-9

Upstream product

• 14021-92-2 2,9-decanediol 
• 478189-32-1 dec-5-yne-2,9-dione 
• 65243-80-3 1,10-dichloro-decane-2,9-dione 
• 108-24-7 acetic anhydride 
• 373-39-7 6-Fluor-hexylmagnesium-chlorid 
• 5978-08-5 1-chloro-4-(1,3-dioxolane)-n-pentane 
• 506-82-1 dimethylcadmium 
• 10027-07-3 suberoyl chloride 
• 75-36-5 acetyl chloride 
• 17036-36-1 hexane-1,6-diyl-bis-magnesium bromide 
• 3884-71-7 bromo-5-pentanone-2 
• 1720-38-3 1,9-decadiyne 
• 20117-47-9 1-methylcyclobutanol 
• 109139-12-0 2-tert-Butylperoxy-1,2-dimethyl-cyclooctanol 

Relevant academic research and scientific papers

Synthesis of new heterocycles containing more than one 1,2,3-thia or selenadiazole rings

(Chemical Equation Presented) The diketones 2a-d with different alkyl chain length are used for the synthesis of di-1,2,3-thia or selenadiazole derivatives 4a-d and 5a-d. The diketones 2a-d where prepared by a unique method through the reaction between the corresponding dibromoalkanes 1a-d and ethyl acetoacetate, which are transformed into the corresponding semicarbazone derivatives 3a-d. The di-1,2,3-thia or selenadiazole derivatives 4a-d and 5a-d were prepared from the semicarbazones derivatives 3a-d on oxidative cyclization with thionyl chloride and selenium dioxide respectively in high yield.

Acylation of unsaturated halides, alcohols, esters and ketones

Treatment of the title compounds with acyl halide and Lewis acid affords unsaturated ketones (mainly α-β with aluminium chloride, selectively β-γ with silver tetrafluoroborate). Reduction of the alkenyl group gives polyfunctional ketones.

Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones

A mimic of the Wacker process for C=O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.

Synthesis of methyl ketones from terminal olefins using PdCl 2/CrO3 system mimicking the Wacker process

An efficient synthesis of methyl ketones from terminal olefins using PdCl2/CrO3 system mimicking the Wacker process is developed. The method shows good functional groups compatibility, no aldehyde by-products and is operationally simple. CrO3 is the sole oxidant and replaces both Cu-salts and molecular oxygen, traditionally used in this process. The method holds potential for future applications in organic synthesis.

Iron(III) sulfate as terminal oxidant in the synthesis of methyl ketones via wacker oxidation

An efficient and environmentally benign method using Fe(III) sulfate as a terminal oxidant in the synthesis of methyl ketones from terminal olefins via the Wacker process is developed. The methodology offers high selectivity for a Markonikov product, shows good functional group compatibility, involves mild reaction conditions, and is operationally simple. Fe2(SO 4)3 is the sole terminal oxidant in this process. The method holds potential for future applications in organic synthesis.

Mild chemo-selective hydration of terminal alkynes catalysed by AgSbF 6

The chemo-selective hydration of a wide range of non-activated terminal alkynes catalysed by AgSbF6 under mild conditions is reported.

Iridium complex-catalyzed addition of water and alcohols to non-activated terminal alkynes

The addition of water and alcohols to non-activated terminal alkynes was found to be promoted by an iridium complex combined with Lewis acid and phosphite. Thus, terminal alkynes reacted with water or alcohols to give ketones or ketals, respectively, in good to excellent yields. α,ω-Diyne like 1,7-octadiyne was converted into 1-(2-methyl-cyclopent-1-enyl)ethanone through the intramoleculer aldol condensation of the resulting 2,7-octanedione induced by Lewis acid.

Samarium diiodide induced reactions of cyclopropyl ketones: Reductive ring cleavage and dimerization leading to 1,8-diketones - Scope, limitations, mechanisms

Reactions of the samarium diiodide/HMPA complex with alkyl cyclopropyl ketones such as 3, 5, and 7 provided dimers incorporating a 1,8-diketone moiety. The products 4, 6, and 8 were isolated in moderate to good yields. The aryl-substituted cyclopropyl ketones afforded a broader product spectrum, which results from the attack of samarium intermediates to the aryl group. Cyclopropyl phenyl ketone (13) gave dimer 14, where one cyclopropane ring was reductively cleaved, whereas the second one is still present. The reductive dimerization of cyclopropyl 2-thienyl ketone (21) furnished the product 22, which still contains two cyclopropyl groups. Further examples demonstrate the diversity of samarium diiodide induced reductions of cyclopropyl ketones. Plausible reaction mechanisms involving samarium ketyl intermediates are presented. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Indium(I) bromide-mediated regioselective Markovnikov hydroselenation, diselenation and hydration of terminal alkynes with diphenyldiselenide in aqueous media

The indium(III) selenolate obtained from indium(I) bromide and diphenyldiselenide promotes, alternatively, the Markovnikov hydroselenation, diselenation or hydration of terminal alkynes, depending on the experimental conditions. Georg Thieme Verlag Stuttgart.

Biomimetic synthesis of symmetric acyclic diketones

A convenient synthetic method for the preparation of symmetric acyclic diketones from dicarboxylic acids is provided. Three bis-benzimidazolium salts were used as tetrahydrofolate coenzyme model, thus the biomimetic synthesis of three symmetric acyclic diketones was successfully accomplished by using the addition-hydrolysis reaction of corresponding bis-benzimidazolium salts with methyl magnesium iodide.