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

Dalton Trans. 2019 Sep 7;48(33):12391-12395. doi: 10.1039/c9dt01359h. Epub 2019 Aug 9.

Authors

Theodore A Gazis¹, Ayan Dasgupta¹, Michael S Hill², Jeremy M Rawson³, Thomas Wirth⁴, Rebecca L Melen¹

Affiliations

¹ Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales CF10 3AT, UK. MelenR@cardiff.ac.uk.
² Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
³ Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, Ontario N9B 3P4, Canada.
⁴ School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales CF10 3AT, UK.

PMID: 31397460
DOI: 10.1039/c9dt01359h

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.