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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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Supplementary files

Article information


Submitted
29 Mar 2019
Accepted
19 Jun 2019
First published
09 Aug 2019

This article is Open Access

Dalton Trans., 2019,48, 12391-12395
Article type
Communication

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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