Photochemical Ring Contraction of 5,5-Dialkylcyclopent-2-enones and in situ Trapping by Primary Amines was written by Jeremias, Noah;Peschel, Martin T.;Jaschke, Constantin;de Vivie-Riedle, Regina;Bach, Thorsten. And the article was included in Journal of Organic Chemistry.Formula: C3H9NO The following contents are mentioned in the article:
If substituted in the 5,5-position, cyclopent-2-enones undergo a smooth photochem. rearrangement to ketenes. A concomitant cyclopropane formation occurs due to a 1,3-shift of the C5 carbon atom from the carbonyl carbon atom (C1) to carbon atom C3. In this study, the cyclopropyl-substituted ketene intermediates were trapped in situ by primary amines providing an efficient entry into 2,2-disubstituted cyclopropaneacetic amides (24 examples, 49-95% yield). A remarkable feature of the reaction is the fact that the photochem. rearrangement can occur from either the first excited singlet (S1) or the resp. triplet state (T1). In line with exptl. results (triplet quenching, sensitization), XMS-CASPT2 calculations support the existence of efficient reaction pathways to the intermediate ketene both on the singlet and on the triplet hypersurface. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Formula: C3H9NO).
2-Methoxyethylamine (cas: 109-85-3) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Formula: C3H9NO
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem