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• W4377819705 endingPage "7069" @default.
• W4377819705 startingPage "7058" @default.
• W4377819705 abstract "By using a quantum-chemical approach, B2PLYP-D2/6-311+G**//B3LYP/6-31+G*, we have carried out a detailed study of the assembly of 1-pyrrolines from N-benzyl-1-phenylmethanimine and phenylacetylene in the superbasic medium KOtBu/dimethyl sulfoxide (DMSO). In this way, we have considered, both theoretically and experimentally, the mechanisms of the assembly through a concerted and stepwise nucleophilic cycloaddition and have addressed the side processes accompanying the assembly. It is found that the assembly via the concerted cycloaddition is kinetically more favorable than that via the stepwise cycloaddition. At the same time, the reaction of C-vinylation of aldimine with phenylacetylene occurs with a similar activation energy as the concerted cycloaddition and leads to the formation of 2-aza-1,4-pentadiene. The anion of 2-aza-1,4-pentadiene is an intermediate for the side processes leading to the formation of triarylpyridines and 1,3-diarylpropan-1-ones. Triarylpyridines are formed through the concerted cycloaddition of the next phenylacetylene molecule to 2-aza-1,4-pentadiene, while 1,3-diarylpropan-1-ones are formed as a result of the hydrolysis of 2-aza-1,4-pentadienes. It is found out that the mild conditions for the assembly of 1-pyrrolines (60 °C, 15 min) relate to the formation of complexes in the KOtBu/DMSO superbasic medium, where the anion is readily accessible for the nucleophilic attack by the phenylacetylene molecule." @default.
• W4377819705 created "2023-05-24" @default.
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• W4377819705 date "2023-05-23" @default.
• W4377819705 modified "2023-10-18" @default.
• W4377819705 title "Quantum-Chemical Study of the Assembly Mechanism of 1-Pyrrolines from <i>N</i>-Benzylaldimines and Arylacetylenes in KO^<i>t</i>Bu/DMSO Superbasic Medium" @default.
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• W4377819705 doi "https://doi.org/10.1021/acs.joc.3c00333" @default.
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