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Issue 48, 2019, Issue in Progress
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Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate

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Abstract

In this paper, the Fries rearrangement of diphenyl carbonate (DPC) catalyzed by organotin compounds with different coordination groups was studied for the first time. The electronic effect and steric hindrance of the coordinating groups were discussed with respect to the reactivity of DPC rearrangement. The results showed that both the electronic effect and steric hindrance of the coordinating groups influenced the acidity of the active tin centers and then affected the catalytic performance of organotin as a Lewis acid for the rearrangement of DPC, and the influence of the electronic effect is greater than that of steric hindrance. The catalytic activity is in the order of BuSnO(OH) > Bu2SnO > Bu2Sn(OCOC11H23)2 > BuSnCl3 > Bu3SnOSnBu3 > Bu3SnCl, and Bu2SnO showed the best catalytic activity due to its strong electron absorption effect, small steric hindrance, and good stability. Under the optimum reaction conditions, the conversion of DPC was up to 93%, and the yields of phenyl salicylate (PS) and xanthone (XA) were 62% and 28%, respectively. In addition, a reaction mechanism of DPC rearrangement catalyzed by the organotin compounds was speculated. This research can provide vigorous theoretical data support to control the byproducts produced by DPC rearrangement in the process of DPC synthesis. It also provides a new route for the preparation of PS and XA.

Graphical abstract: Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate

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Publication details

The article was received on 14 Jul 2019, accepted on 29 Aug 2019 and first published on 06 Sep 2019


Article type: Paper
DOI: 10.1039/C9RA05390E
RSC Adv., 2019,9, 28112-28118
  • Open access: Creative Commons BY-NC license
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    Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate

    T. Liu, X. Yuan, G. Zhang, Y. Zeng, T. Chen and G. Wang, RSC Adv., 2019, 9, 28112
    DOI: 10.1039/C9RA05390E

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