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Reactions of hydrazones and hydrazides with Lewis acidic boranes

Gazis, Theodore A., Dasgupta, Ayan, Hill, Michael S., Rawson, Jeremy M., Wirth, Thomas and Melen, Rebecca L. 2019. Reactions of hydrazones and hydrazides with Lewis acidic boranes. Dalton Transactions (33) , pp. 12391-12395. 10.1039/C9DT01359H

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Royal Society of Chemistry
ISSN: 1477-9226
Funders: EPSRC
Date of First Compliant Deposit: 16 August 2019
Date of Acceptance: 19 June 2019
Last Modified: 30 Nov 2019 06:37
URI: http://orca-mwe.cf.ac.uk/id/eprint/124967

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