3156-76-1

Upstream product

• 463-51-4 Ketene 
• 3156-73-8 2-hydroxy-1-nitropropane 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 187737-37-7 propene 
• 108-05-4 vinyl acetate 
• 3156-73-8 (+)-1-nitro-2-propanol 

Downstream Products

• 141367-68-2 2-(2-Benzyloxy-phenyl)-4-methyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 141367-73-9 2-(2-Benzyloxy-phenyl)-1-cyclohexyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 141367-69-3 2-(2-Benzyloxy-phenyl)-1-(3,5-dimethyl-phenyl)-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 17082-05-2 (E)-1-nitroprop-1-ene 
• 27675-36-1 1-nitropropene 
• 66448-56-4 (β-nitro-isopropyl)-phenyl sulfide 
• 62786-72-5 benzyl 4-methylpyrrole-2-carboxylate 

Relevant academic research and scientific papers

Effect of solvent structure on enantioselectivity of lipase-catalyzed transesterification

Enantioselectivity in transesterification of a secondary alcohol under lipase-catalysis is largely affected by the solvent used. Two groups of solvents, cyclic and acyclic, show different feature on enantioselectivity.

Synthesis of Norbornanones with a Geminal Dimethyl Group

The synthesis of gem-dimethylnorbornanones is described.One synthetic pathway after a Diels-Alder reaction involves the transformation of the nitro group into the oxo group with subsequent methylation into the geminal dimethyl product.A shorter way by -cycloaddition of cyclopentadiene with a suitable dimethylated dienophile (e.g. 2-methyl-1-nitropropene) failed, probably by steric hindrance of the dienophile. 7-Oxanorbornanones with a gem -dimethyl group could not be prepared.A second synthetic approach to gem-dimethylnorbornanones is opened by Lewis acid catalyzed rearrangement of cyclohexenylcarbaldehydes. - Keywords: Camphenilone; Diels-Alder reaction; Homonorbornanone; α-Methylation of carbonyls; Nef-reaction; Norepifenchone

The Electronic Interaction between the Methyl Group and Trigonal Carbon

The nature of the interaction between methyl and a trigonal carbon has been examined by the effect of substituents on the methyl rotational barrier.Barriers have been measured for para-substituted toluenes and for cis- and trans-substituted propenes by the motional effects of methyl rotation on dipole-dipole spin-lattice relaxation.The toluene barriers exhibit a fair correlation with ?I and a very poor one with ?R.Thus hyperconjugation cannot be a major factor in determining the methyl rotational barrier.The propene barriers, particularly in the cis series, also correlate with ?I but have a better correlation with ?R than do the toluenes.Examination of all the 13C chemical shifts showed that the rotational barriers correlate only with the ortho carbon in the toluenes and with the 2-carbon (methyl substituted) in the propenes.These results suggest that the methyl rotational barrier is primarily sensitive to the nature of the ortho C-H bond in the toluenes and the α-C-H bond in the propenes.The ?R and ?I correlations are in accord with this model, since the ortho toluene carbon cannot interact directly through resonance with the para substituent but must depend on polar interactions.In the propenes, on the other hand, electron density at the α-carbon is determined by both inductive and resonance effects.The major factor in determining these barriers is the electron density at the critical carbon center, which is the ortho carbon for the toluenes and the α-carbon for the propenes.