Chemistry can be defined as the study of matter and the changes it undergoes. You¡¯ll sometimes hear it called the central science because it is the connection between physics and all the other sciences, starting with biology. 83411-71-6, Name is Bis(2,4,4-trimethylpentyl)phosphinic acid, molecular formula is , belongs to pyrrolines compound. In a document, author is Kim, Wan Shin, Safety of Bis(2,4,4-trimethylpentyl)phosphinic acid.
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.
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 83411-71-6, in my other articles. Safety of Bis(2,4,4-trimethylpentyl)phosphinic acid.
Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem