Reference of 10191-41-0, Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. 10191-41-0, Name is DL-alpha-Tocopherol, SMILES is CC1=C2C(OC(CCCC(CCCC(CCCC(C)C)C)C)(C)CC2)=C(C(C)=C1O)C, belongs to pyrrolines compound. In a article, author is Kim, Wan Shin, introduce new discover of the category.
Mechanistic Investigation of the Formation of Isoindole N-Oxides in the Electron Transfer-Mediated Oxidative Cyclization of 2 ‘-Alkynylacetophenone Oximes
This paper describes a joint experiment-theory investigation of the formation and cyclization of 2’-alkynylacetophenone oxime radical cations using photoinduced electron transfer (PET) with DCA as the photosensitizer. Using a combination of experimental H-1 and C-13 nuclear magnetic resonance (NMR) spectra, high-resolution mass spectrometry, and calculated NMR chemical shifts, we identified the products to be isoindole N-oxides. The reaction was found to be stereoselective; only one of the two possible stereoisomers is formed under these conditions. A detailed computational investigation of the cyclization reaction mechanism suggests facile C-N bond formation in the radical cation leading to a 5-exo intermediate. Back-electron transfer from the DCA radical anion followed by barrierless intramolecular proton transfer leads to the final product. We argue that the final proton transfer step in the mechanism is responsible for the stereoselectivity observed in experiment. As a whole, this work provides new insights into the formation of complex heterocycles through oxime and oxime ether radical cation intermediates produced via PET. Moreover, it represents the first reported formation of isoindole N-oxides.
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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem