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Gas‐phase synthesis of hydrodiphenylcyclopropenylium via nonclassical Favorskii rearrangement from alkali‐cationized α,α′‐dibromodibenzyl ketone
Author(s) -
Zhao ZhiXiong,
Wang HaoYang,
Xu Chu,
Guo YinLong
Publication year - 2010
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.4694
Subject(s) - chemistry , alkali metal , ketone , protonation , electrospray ionization , dissociation (chemistry) , mass spectrometry , lewis acids and bases , medicinal chemistry , inorganic chemistry , organic chemistry , ion , chromatography , catalysis
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.