Reactions of hydrazones and hydrazides with Lewis acidic boranes

Gazis, Theodore A., Dasgupta, Ayan, Hill, Michael S., Rawson, Jeremy M., Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 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:	06 Aug 2023 10:05
URI:	https://orca.cardiff.ac.uk/id/eprint/124967

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