В журнале JOC - The Journal of Organic Chemistry (IF 3,3) опубликована статья, соавторами каторой являются сотрудники лаборатории магнитной радиоспектроскопии к.х.н., снс А.М. Генаев и cнс Г.Е. Сальников
Triflic Acid-Mediated Condensation of Phthalimide with Diaryl Ethers as a Route to Spiro-Isoindolinones: Mechanistic Insights and Related Reactions
Alexander M. Genaev, George E. Salnikov, Konstantin Yu. Koltunov
J. Org. Chem., 2024, 89, 21, 15931-15940
Published on 16 August 2024
doi: 10.1021/acs.joc.4c02139
Abstract
Phthalimide and N-phenylphthalimide smoothly condense with di-p-tolyl ether in triflic acid (CF3SO3H, TfOH) to obtain the corresponding spiro[isoindoline-1,9′-xanthen]-3-ones. Structural analogs of phthalimide, such as phthalic anhydride and 1,3-indandione (but not saccharin), show similar reactivity. In contrast, N-(tetrafluoropyridin-4-yl)phthalimide reacts with DTE by an alternative pathway, yielding isobenzofuran dispiro derivative. The mechanistic aspects of these reactions are discussed on the basis of in situ NMR and theoretical (DFT) studies, providing insights on the key intermediacy of O,O-diprotonated forms of the starting compounds.
