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The participation of oleic acid and its esters in [3+2] cycloaddition reactions: a mini-review

Dresler Ewa

Scientiae Radices

2024

Vol. 3, Iss. 1

53--61

This mini review presents the state of knowledge on the [3+2] cycloaddition reactions involving fatty acids and their esters with triatomic components (TAC). In general, the literature reports are quite sparse and relatively old. The reaction yield was in the range of 12-85%. The best result of 32CA was obtained from the reaction of butylonitrile N-oxide (4) and methyl oleate (2). Other tested TAC as components of title reactions were nitrylimines and ozone.

Sterical index: a novel, simple tool for the interpretation of organic reaction mechanisms

Dresler Ewa, Allnajar Radwan, Jasiński Radomir

Scientiae Radices

2023

Vol. 2, Iss. 1

69--74

A new, simple index for the quantitative description of steric effects was proposed based on the results of DFT calculations. This effect was connected with the disturbance of synchronicity within transition states of the model Diels-Alder reaction. The obtained results offer the possibility of predicting steric effects determined by alkyl groups for a wide range of bimolecular processes.

Polar [3+2] cycloaddition between N-methyl azomethine ylide and trans-3,3,3-trichloro-1-nitroprop-1-ene

Żmigrodzka Magdalena, Sadowski Mikołaj, Kras Jowita, Dresler Ewa, Demchuk Oleg M., Kula Karolina

Scientiae Radices

2022

Vol. 1, Iss. 1

26--35

Pyrrolidines are important heterocyclic organic compounds which show biological effects. Many of them are successfully used in medicine. These compounds can also be applied in industry, for example as dyes or agrochemical substances. Therefore, the study of pyrrolidines chemistry is important for modern science. In this paper the pyrrolidines synthesis in [3+2] cycloaddition between Nmethyl azomethine ylide and trans-3,3,3-trichloro-1-nitroprop-1-ene was studied. The reaction was carried out experimentally and based on computational research. The obtained results show the reaction may be of a polar nature, and proceed under mild conditions leading to (3SR,4RS)-1-methyl-3-nitro-4-(trichloromethyl)pyrrolidine as a single reaction product. Probably, a similar protocol can be applied for analogous reactions involving other 2-substituted nitroethene analogues.