92862-83-4

Upstream product

• 108-94-1 cyclohexanone 
• 127084-26-8 1-butyltelluro-1-phenyl ethene 
• 521275-61-6 1-(1-phenylvinyl)cyclohexyl hydroperoxide 
• 55983-32-9 2-methyl-2-phenylmethylenecyclohexane 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 98-81-7 1-bromovinylbenzene 
• 712-50-5 Cyclohexyl phenyl ketone 
• 67300-99-6 1-phenylethenylmagnesium bromide 

Downstream Products

• 96748-61-7 (1-(cyclohex-1-en-1-yl)vinyl)benzene 
• 1263406-32-1 2-(cyclohexanol-1-yl)-2-phenyloxirane 

Relevant academic research and scientific papers

Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen

Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper-catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4-dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.

A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement

A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20?:?1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.

Synthesis of Macrocyclic Ketones through Catalyst-Free Electrophilic Halogen-Mediated Semipinacol Rearrangement: Application to the Total Synthesis of (±)-Muscone

A series of macrocycles were successfully prepared using electrophilic halogen-mediated semipinacol rearrangement under mild conditions. Although the expansion from small ring to medium ring is an energetically unfavorable process, the electrophilic halog

Synthesis of functionalized epoxides by copper-catalyzed alkylative epoxidation of allylic alcohols with alkyl nitriles

A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp3)-O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted epoxides via formation of a C(sp3)-C(sp3) and a C(sp3)-O bond with moderate to excellent diastereoselectivity.

Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate

Treatment of 1-methyl-2-methylene-1-cyclohexyl hydroperoxide with a mixture of FeSO4/CuCl2 yielded 1-(1-chlorocyclohexyl)ethanone as the major product consistent with 6-endo-trig cyclization of the intermediate 5-acetylhex-5-enyl rad

AlEt3-promoted eliminative ring-opening of β-hydroxy epoxides: Highly stereoselective synthesis of terminal α-hydroxy olefins

AlEt3-promoted eliminative ring-opening of β-epoxy alcohols leading to α-hydroxy olefins is reported. This eliminative ring-opening reaction is shown to be highly stereoselective, thus providing an alternative asymmetric synthesis for α-hydroxy olefins.

Selectivity on the reaction of vinylic tellurides with butyllithium in the presence of carbonyl compounds.

The treatment of isomeric vinylic tellurides 5-7 with butyllithium in THF at -78 °C in the presence of a carbonyl compound such as benzaldehyde or cyclohexanone was studied. High selectivity of the attack at the tellurium atom was observed. In most cases, the corresponding allylic alcohol was obtained as the only (or major) product instead of the alcohols derived by the 1,2 addition of BuLi at the carbonyl compound. Similar results were obtained using the ketenetelluroacetal 14 instead of the vinylic monotellurides.