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Issue 33, 2019
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Reactions of hydrazones and hydrazides with Lewis acidic boranes

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Abstract

The reaction of (diphenylmethylene)hydrazone or 1,4-bis-hydrazone-ylidene(phenylmethyl)benzene with Lewis acidic boranes B(2,4,6-F3C6H2)3 or B(3,4,5-F3C6H2)3 generates the Lewis acid–base adducts. Alternatively, when (9H-fluoren-9-ylidene)hydrazone is employed several products were isolated including 1,2-di(9H-fluoren-9-ylidene)hydrazone, the 2 : 1 borane adduct of NH2–NH2 and the 1-(diarylboraneyl)-2-(9H-fluoren-9-ylidene)hydrazone in which one ArH group has been eliminated. The benzhydrazide starting material also initially gives an adduct when reacted with Lewis acidic boranes which upon heating eliminates ArH generating a CON2B heterocycle.

Graphical abstract: Reactions of hydrazones and hydrazides with Lewis acidic boranes

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Publication details

The article was received on 29 Mar 2019, accepted on 19 Jun 2019 and first published on 09 Aug 2019


Article type: Communication
DOI: 10.1039/C9DT01359H
Dalton Trans., 2019,48, 12391-12395
  • Open access: Creative Commons BY license
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    Reactions of hydrazones and hydrazides with Lewis acidic boranes

    T. A. Gazis, A. Dasgupta, M. S. Hill, J. M. Rawson, T. Wirth and R. L. Melen, Dalton Trans., 2019, 48, 12391
    DOI: 10.1039/C9DT01359H

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