Reactions of hydrazones and hydrazides with Lewis acidic boranes

Theodore A. Gazis; Ayan Dasgupta; Michael S. Hill; Jeremy M. Rawson; Thomas Wirth; Rebecca L. Melen

doi:10.1039/c9dt01359h

Reactions of hydrazones and hydrazides with Lewis acidic boranes

Theodore A. Gazis, Ayan Dasgupta, Michael S. Hill, Jeremy M. Rawson, Thomas Wirth, Rebecca L. Melen

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (SciVal)

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.

Original language	English
Pages (from-to)	12391-12395
Number of pages	5
Journal	Dalton Transactions
Volume	48
Issue number	33
Early online date	9 Aug 2019
DOIs	https://doi.org/10.1039/c9dt01359h
Publication status	Published - 7 Sept 2019

Funding

T. A. G. thanks the EPSRC Cardiff/Bristol/Bath CDT in Catalysis for funding (EP/L016443/1). A. D. and R. L. M. would like to acknowledge the EPSRC for an Early Career Fellowship for funding (EP/R026912/1). J. M. R. thanks NSERC for financial support.

ASJC Scopus subject areas

Inorganic Chemistry

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Cite this

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title = "Reactions of hydrazones and hydrazides with Lewis acidic boranes",

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.",

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T1 - Reactions of hydrazones and hydrazides with Lewis acidic boranes

AU - Gazis, Theodore A.

AU - Dasgupta, Ayan

AU - Hill, Michael S.

AU - Rawson, Jeremy M.

AU - Wirth, Thomas

AU - Melen, Rebecca L.

PY - 2019/9/7

Y1 - 2019/9/7

N2 - 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.

AB - 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.

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EP - 12395

JO - Dalton Transactions

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ER -

Reactions of hydrazones and hydrazides with Lewis acidic boranes

Abstract

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ASJC Scopus subject areas

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