The possibility of the preparation of free 1,1-dinitroethene was examined experimentally on the basis of procedures described earlier for other examples of 1-R-1-nitroethenes. It was found, that these types of protocols are non-usable for the preparation of the title compound due to its high reactivity and tendency to decomposition and oligomerization.
[3+2] cycloaddition reactions of -COOMe and -CN trans-substituted nitroethenes with (Z)-C,N-diphenylimine N-oxide were tested. For the contrast to most known nitroalkene/nitrone cycloaditions, the reactions studied realized with the formation of 5-nitroisoxazolidines.
The possibility of the construction of five-membered heterocycles, including single heteroatom or systems with two, three and four heteroatoms were critically reviewed based on the recent reports regarding to the [3+2] cycloaddition reactions. Almost all of analysed reaction are realized with high regio- and stereoselectivity.
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.
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