Gas‐phase synthesis of hydrodiphenylcyclopropenylium via nonclassical Favorskii rearrangement from alkali‐cationized α,α′‐dibromodibenzyl ketone |
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Authors: | Zhi‐Xiong Zhao Hao‐Yang Wang Chu Xu Yin‐Long Guo |
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Affiliation: | Shanghai Mass Spectrometry Center, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P.R. China |
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Abstract: | The gas‐phase synthesis of hydrodiphenylcyclopropenylium from alkali‐cationized α,α′‐dibromodibenzyl ketone (1) via nonclassical Lewis‐acid‐induced Favorskii rearrangement has been studied by electrospray ionization/tandem mass spectrometry (ESI‐MS/MS) and theoretical methods, showing that cations [1–Br]+ by debromination from 1 and 1 · M+(M = Li or Na) by alkali‐metal cationization of 1 could convert into the protonated diphenylcyclopropenone 2 · H+ by collision‐induced dissociation in the gas phase. A concerted mechanism for the Lewis‐acid‐induced Favorskii rearrangement from alkali‐metal‐cationized α,α′‐dibromodibenzyl ketone was proposed and studied, based on mass spectrometric results and theoretical methods. Copyright © 2010 John Wiley & Sons, Ltd. |
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