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.
Highlights
The reaction ofhydrazone 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
The benzhydrazide starting material initially gives an adduct when reacted with Lewis acidic boranes which upon heating eliminates ArH generating a CON2B heterocycle
The ability of transition metal complexes to bind to N2 has been attributed to the roles of the metal d-orbitals in bonding and back-bonding interactions with N2.1 Recently the activation of nitrogen–nitrogen bonds such as azides, diazo-compounds, hydrazones and dinitrogen using boranes has gained momentum.[2,3]
Summary
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. Reactions of hydrazones and hydrazides with Lewis acidic boranes†
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