24580-51-6

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 107-05-1 3-chloroprop-1-ene 
• 107-18-6 allyl alcohol 
• 75863-14-8 2-Propenyltitanium triisopropoxide 
• 106-95-6 allyl bromide 
• 7393-43-3 tetraallyl tin 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 55047-00-2 cis-1-(3-hydroxypropyl)-2-methylcyclohexanol 
• 55047-00-2 trans-1-(3-hydroxypropyl)-2-methylcyclohexanol 
• 855414-85-6 (1-hydroxy-2-methyl-cyclohexyl)-acetaldehyde 
• 7071-16-1 (2-methyl-cyclohexyliden)-acetaldehyde 
• 105463-30-7 (2-methyl-cyclohex-1-enyl)-acetaldehyde 

Relevant academic research and scientific papers

SELECTIVE ALLYLATION OF CARBONYL COMPOUNDS IN AQUEOUS MEDIA

The use of aqueous neutral media leads to excellent yelds of homoallylic alcohols from reactions of allyl halides with carbonyl compounds in the presence of tin or zinc.The stereochemical course and range of application of this reaction have been investigated.

Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds

The reaction of the allyl indium sesquibromide (CH2 =CHCH2)3In2Br3 with four equivalents of a bulky lithium alkoxide ((CH3)3COLi or (CH3)3CCH2OLi) results in modified reagents which show unusual degrees of chemo-and stereoselectivity in reactions with carbonyl compounds. For example, in reactions with cyclohexanone derivatives, 84-93% equatorial attack with preferential formation of the axial alcohols is observed. Chiral aldehydes react in a highly diastereoselective manner.

Preparation method and application of 2-hydroxymethyloxetane derivative

The invention discloses a preparation method and application of a 2-hydroxymethyloxetane derivative. The method comprises the following steps that a compound II and a compound III are used as raw materials; Barbier reaction is performed to obtain a compound IV; olefinic bonds in the compound IV are cyclized and oxidized to obtain a compound V; under the alkaline condition, ring opening is performed to generate a compound VI; after ring closing reaction, a compound VII is obtained; finally, benzyl protecting groups are removed to obtain the 2-hydroxymethyloxetane derivative (the compound I).

[Bmim] [Br] as a solvent and activator for the ga-mediated barbier allylation: Direct formation of an N -heterocyclic carbene from Ga metal

The room-temperature ionic liquid (RTIL) [bmim][Br] has been found to be an excellent green and inexpensive medium for the Ga-mediated allylation of aromatic and aliphatic aldehydes and ketones. The RTIL activated the metal via formation of a Ga-N-heteroc

Barbier allylation of aldehydes and ketones with aluminium and catalytic indium metal: An economical alternative

An economical preparative protocol for the Barbier allylation of aldehydes and ketones in DMF, using aluminium foil in the presence of a catalytic amount of indium metal, is reported. All yields obtained are in general similar but slightly lower than those reported for the stoichiometric indium allylation. Aluminium alone failed to give rise to any detectable product. ARKAT-USA, Inc.

Granular indium Barbier allylation of carbonyl compounds: A more economical protocol

A new protocol, amenable to be used in large-scale preparations, using a cheaper form of indium metal and mild warming is reported for the Barbier allylation of aldehydes and ketones with allyl bromide in N,N-dimethylformamide. Georg Thieme Verlag Stuttgart.

Ceric(IV) ammonium nitrate: A novel reagent for the synthesis of homoallyl alcohols

A rapid and highly efficient method has been developed for the allylation of aldehydes with allyltributylstannane using a catalytic amount of eerie ammonium nitrate in acetonitrile under mild and neutral conditions to afford the corresponding homoallyl al

Zinc mediated allylation of aldehydes and ketones using allyl bromides and commercial zinc dust. the issue of regio- And stereoselectivity

An efficient procedure for the preparation of homoallylic alcohols has been achieved by a simple reaction of an aldehyde or a ketone with allyl bromide and commercial zinc dust in tetrahydrofuran. Excellent regioselectivity has been observed in the reaction of substituted allyl bromides.

Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions

The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a domi

Palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2

Allylic alcohols can be applied to carbonyl allylation via the formation of π-allylpalladium complexes, using palladium as catalyst and SnCl2 as a reducing agent. This reaction has chemoselectivity: The reactivity order of allylating agents is allylic carbonate > allylic alcohol > allylic acetate, and that of carbonyl compounds is aldehyde > ketone. High regioselcction was observed in polar solvents such as DMF, DMI, and DMSO; carbonyl compounds apparently attacked the more substituted allylic position of π-allylpalladium complexes to afford only one regioisomer. Diastereocontrol in the carbonyl allylation of aromatic aldehydes by (E)-2-butenol was achieved by the choice of polar solvents; use of DMSO at 25 °C led to syn selection, while anti selection was found at -10 °C in THF. The addition of H2O in any solvent accelerated the carbonyl allylation and enhanced both regioselectivity and the diastereoselectivity. Anti selection in DMF, DMI, and THF-H2O can be explained by the chair form of the six-membered cyclic transition state, while syn selection in DMSO allows us to propose an acyclic antiperiplanar transition state. An NMR spectroscope investigation demonstrated that the actual allylating agent in dry medium was allyltrichlorotin: 1H, 13C, and 119Sn NMR spectra of the reaction of allyl alcohol with PdCl2(PhCN)2-SnCl2 in DMF-d7. corresponded to those of the reaction of allyl chloride with PdCl2(PhCN)2-SnCl2 in DMF-d7.