28817-29-0

Upstream product

• 108-94-1 cyclohexanone 
• 108-85-0 1-bromocyclohexane 
• 623-43-8 methyl crotonate 
• 623-43-8 crotonic acid methyl ester 
• 626-62-0 Cyclohexyl iodide 
• 110-82-7 cyclohexane 
• 90334-41-1 N-Cyclohexylidene-N'-trityl-hydrazine 

Relevant academic research and scientific papers

A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Nickel Boride (cat.) - Borohydride Exchange Resin in Methanol

The radical addition reaction of alkyl iodides with α,β-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50-95%) using Ni(OAc)2 (0.05-0.2 equiv) - BER (3-5 equiv) in methanol in 1-9 h at room temperature or at 65°C. Nickel boride on borohydride exchange resin (BER) is a good alternative reagent to tributyltin hydride for the coupling of alkyl iodides with the electron deficient alkenes in methanol. Compared with tributyltin hydride method, this method has an advantage of simple workup, since nickel boride - BER can be removed readily by filtration.

A Radical Carbon-carbon Bind Forming Reaction: Indium Mediated Radical Addition to β-Substituted Conjugated Alkenes in Aqueous Media

Indium-mediated 1,4-addition of alkyl radical to β-substituted conjugated alkenes in aqueous media has been developed. The reaction affords 1,4-addition products to various α,β-enones regiospecifically in high isolated yields.

A new coupling reaction of alkyl iodides with α,β-unsaturated esters using Ni2B(cat.)-BER in methanol

Alkyl iodides can be coupled with α,β-unsaturated esters using Ni2B(0.05-0.2 eq)-BER(3 eq) in methanol at room temperature. Products (68-95%) are conveniently isolated, simply filtering the resin and evaporating the excess enoates and methanol.

PHOSPHINE NICKEL COMPLEX AS CATALYST IN REACTIONS OF ORGANIC BROMIDES RBr WITH α,β-UNSATURATED KETONES, NITRILES, AND ESTERS. CONJUGATE ADDITION OF R GROUP AND H ATOM ACROSS THE C=C BOND

Reactions of organic bromides, particularly of secondary and tertiary alkyl bromides, with α,β - unsaturated carbonyl compounds and acrylonitryle in the presence of the catalytic system nickel complex-zinc result in formation of products of conjugate addition of the organic moiety of the bromide and a hydrogen atom across the C=C double bond of the unsaturated substrate.

BIS(TRI-n-BUTYLSTANNYL)BENZOPINACOLATE: PREPARATION AND USE AS A MEDIATOR OF INTERMOLECULAR FREE RADICAL REACTIONS

Bis(tri-n-butylstannyl)benzopinacolinate (2) serves as a thermal source of tri-n-butylstannyl radicals and mediates intermolecular coupling of selected alkyl halides to O-benzylformaldoxime and electron deficient olefins.A free radical non-chain mechanism is proposed for these reactions.

AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.

The lithium salts of trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.

Thermal Addition of Alkanes to Alkenes, IV. Regioselectivity in the Addition of Cyclohexane to 1,2-Disubstituted Alkenes

Alkanes can be added to alkenes in a free radical chain reaction ("ane reaction").Regioselectivity in the addition of cyclohexane to (E)-3-alkyl substituted methyl acrylates have been measured at 300-450C.The ratio of the two regioisomers 3 and 4 shows a correlation with steric substituent constants Es.Relative rates of the addition of cyclohexyl radical to the alkene and β-scission of the adduct radical versus H-transfer from cyclohexane are determining the ratio of the regioisomers.A minor temperature dependence of regioselectivity has been observed.In relation to the products 3 and 4, ane reaction at a temperature of 450C can be more selective than radical addition reaction at room temperature.Regioselectivity of the addition of cyclohexane to methyl cinnamate at 360-420C shows a slight polar substituent effect.Electron withdrawing substituents have been shown to increase product ratio 4/3.

Michael Additions of Hydrazones for Carbon-Carbon Bond Formation

The lithium salts of t-butyl- and trityl-hydrazones react with methyl crotonate to form C-trapped azo-esters and similar products were observed from a thermal ene-reaction of aldehyde t-butylhydrazones with methyl acrylate or acrylonitrile, and aldehyde phenylhydrazones with methyl acrylate; these products can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, saturated esters, γ-alkyl-2-pyrrrolidones, and γ-amino-esters.

HOCHDRUCK-HOCHTEMPERATUR-REAKTIONEN IN EINEM STROEMUNGSREAKTOR-VI. THERMISCHE ADDITION VON ALKANEN AN ALKENE

The thermal Anti-Markownikow-addition of alkanes to activated and desactivated alkenes ("direkte substituierende Addition", "Ane-reaction") at 650-723 K and reaction times of 1-10 min. is described.