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CARBON CHAIN ELONGATION FACILITATED BY THE REPULSIVE COULOMB FORCE BETWEEN TWO GAS-PHASE CATIONS

Xiaoping ZHANG  Keke HUANG  Yuanyuan CHENG  Xiang REN  Honghan CHEN  Yufen WANG  Shouhua FENG  Huanwen CHEN  
【摘要】:Establishing new strategies for carbon chain elongation(CCE) and advanced functional group construction is of sustainable interest. Accelerated in vacuum(~10-5 Torr) by a waveform(~300 kHz), a bared sodiated acetone(A, m/z 81) can closely approach to another one(B, m/z 81) for CCE reaction, in which the elimination of a methyl cation and the coupling of two carbonyl carbon groups simultaneously occurred to produce sodium 2-methyl-butane-2,3-diolate)-3-ium(m/z 147). The multistage tandem high-resolution mass spectrometry measurements, deuterium labeling experiments, and theoretical calculations support that the repulsive Coulomb force between the bared ions A and B is significantly larger than the cleavable bond energy, facilitating the CCE reaction. Similarly, the demethylation/deamination C–C coupling was observed for protonated/sodiated acetone, butanone, 2-pentanone, 2-hexanone, urea, and acetic acid, providing a validated alternative strategy for CCE and advanced functional group construction.

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