74221-87-7

Upstream product

• 2562-37-0 1-nitrocyclohexene 
• 98-80-6 phenylboronic acid 
• 2996-92-1 phenyl trimethylsiloxane 
• 2783-14-4 2-nitro-1-octene 
• 96-10-6 diethylaluminium chloride 
• 24347-65-7 4-nitro-5-phenyl-Δ'-cyclohexene 

Downstream Products

• 5554-79-0 (+/-)-1-aci-1-nitro-2-phenyl-cyclohexane 
• 17448-50-9 cis-1-nitro-2-phenylcyclohexanone 
• 74221-93-5 N-hydroxy-7-phenyl-ε-caprolactam 

Relevant academic research and scientific papers

Deoxycholic acid-derived biaryl phosphites as versatile and enantioselective ligands in the rhodium-catalyzed conjugate addition of arylboronic acids to nitroalkenes

A highly enantioselective conjugate addition of arylboronic acids to cyclic as well as acyclic aromatic and aliphatic nitroalkenes is presented. The rhodium complexes obtained from deoxycholic acid-derived binaphthyl and flexible biphenyl phosphites showed good activity as well as very high enantioselectivity (ee up to 99%) in the conjugated addition even in the presence of challenging substrates such as 1-nitrocyclohexene or aliphatic acyclic nitroalkenes. Copyright

Palladium(II)-catalyzed conjugate addition of arylsiloxanes in water

Equation Presented Palladium-phosphinous acids catalyze the conjugate addition of arylsiloxanes to a wide range of α.β-unsaturated substrates in water microwave-assisted procedure is described that uses 5 mol % of POPd1 to afford /-substituted ketones, aldehydes, esters, nitriles, an nitroalkanes in 83% to 96% yield within 4 h. This method eliminates the need for stoichiometric additives and an excess of arylsiloxane, an does not require an inert atmosphere.

ω-Alkenyl α-Nitroalkyl Radicals. Part 3. Radical Chain Reactions of ω-Alkenyl α-Halogenonitroalkanes

SRN1 reactions between 5-bromo-5-nitrohex-1-ene and the nitronate anions of 2-nitropropane and 5-nitrohex-1-ene failed to give cyclisation of the intermediate α-nitroalkyl radical onto the alkene.Reaction between exo-5-bromo-endo-5-nitro-exo-6-phenylbicyclohept-2-ene 1 and the anion of 2-nitropropane did not undergo an SRN1 reaction and Br+ abstraction gave 2-bromo-2-nitropropane and 5-endo-nitro-exo-6-phenylbicyclohept-2-ene.BNAH reduction of exo-5-bromo-endo-5-nitro-exo-6-phenylbicyclohept-2-ene 1, 6-bromo-6-nitrohept-1-ene, and 1-bromo-1-nitro-2-(prop-2-enyl)cyclohexane gave the corresponding nitroalkanes without any cyclosation of the intermediate α-nitroalkyl radicals.Initial results indicate that an iodine atom transfer methodology provides a possible general method for the cylisation of ω-alkenyl α-nitroalkyl radicals.Cyclisation of intermediate α-nitroalkyl radicals, generated by photolysis of 1-(bicyclohept-5-en-endo-2-yl)-2-iodo-2-nitropropane 5a, gave a good yield of two diastereomeric tricyclic iodonitro compounds 6a and 7a.Photolysis of 1-(bicyclohept-5-en-endo-2-yl)-2-iodo-2-nitroethane 5b and 2-(but-3-enyl)-1-iodo-1-nitrocyclohexane 11 also gave the expected products from 5-exo cyclisation of the intermediate α-nitroalkyl radicals.The tricyclic iodonitro compound 6a was synthesised from the corresponding endo-methanesulfonate 15, the structure of which was determined by X-ray crystallography.

Nitro Olefins and Organoaluminum Compounds: A Powerful Synthetic Tool in Organic Chemistry

M species react with α-nitro olefins showing an unusual aptitude for a preferential transfer of saturated alkyl groups; M (R' = phenyl, benzyl, allyl) species, on the other hand, are able to transfer unsaturated groups with high chemosele