27675-36-1

Upstream product

• 3156-73-8 2-hydroxy-1-nitropropane 
• 3156-76-1 2-acetoxy-1-nitropropane 

Downstream Products

• 17082-05-2 (E)-1-nitroprop-1-ene 
• 112672-95-4 (2R,3R,3aR)-6,6-Dimethyl-3-nitro-2-phenyl-hexahydro-pyrrolo[1,2-b]isoxazole 
• 76512-42-0 1-(4-butylphenyl)propan-2-one 
• 2562-37-0 1-nitrocyclohexene 
• 20320-20-1 4-benzyl-1-(4-fluorophenyl)-1H-1,2,3-triazole 
• 21443-88-9 5-methyl-4-nitro-1-phenyl-1H-[1,2,3]triazole 
• 6111-96-2 5-methyl-1-phenyl-1H-1,2,3-triazole 
• 4749-28-4 2-nitropropene 
• 15922-53-9 1,5-dimethyl-1H-[1,2,3]triazole 
• 60166-43-0 1,4-dimethyl-1H-[1,2,3]triazole 

Relevant academic research and scientific papers

STEREOSPECIFICITY OF 1,3-DIPOLAR CYCLOADDITIONS OF CYCLIC NITRONES TO (E) and (Z)-β-NITROSTYRENES

3,4-Dihydroisoquinoline-N-oxide (1) reacted readily with (E)-β-nitrostyrene in a regiospecific reaction to give a mixture of 4-nitro-5-phenylisoxazolidines 3a and 4a resulting from endo and exo (with respect to the nitro group) transition states, respectively.This cycloaddition was found reversible under mild conditions.A careful study disclosed >= 99.89percent stereoselectivity thus narrowly circumscribing the possibility of stereochemical leakage over the cycloaddition and cycloreversion processes.Moreover, our experimental data showed that eventual loss of stereochemistry should be ascribed to base catalysed isomerizations in the adducts and/or educts.The reaction of 1 with (Z)-β-nitrostyrene (exo specific and regiospecific) turned out to be faster than that of the (E)-isomer.This is the first example of higher reactivity of a cis than a trans-alkene in 1,3-dipolar cycloadditions.The endo-trans adduct 3a cycloreverted faster than the exo-trans isomer 4a which in turn underwent fragmentation more readily than the exo-cis 6a.The cycloreversion rate was slightly enhanced by increased solvent polarity.This study was extended to the reaction of 5,5-dimethylpyrroline-N-oxide with both the cited dipolarophiles.

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.