Monocarbaborane anion chemistry: use of an anilinyl residue as an anchor group for the construction of rod-like monocarbaboranyl diazo and imino compounds

Reaction of the [1-(4-H2N–C6H4)-closo-1-CB9H9]− anion 1 with Me2CHCH2CH2ONO and dilute HCl gives neutral [1-(4-N2–C6H4)-closo-1-CB9H9] 3, which reacts with PhNH2 to form the 19.5 Å [1-{4-(4-H2N–C6H4–NN)–C6H4}-closo-1-CB9H9]− azo anion 2. Anion 1 with ketones and aldehydes gives imino compounds: with (CH3)2CO it gives neutral [1-{4-(Me2CNH)–C6H4}-closo-1-CB9H9] 6 and with the para-dialdehyde C6H4-1,4-(CHO)2 it gives the 30.5 Å extended rod-like neutral species [C6H4-1,4-{1-(CHNH–C6H4)-closo-1-CB9H9}2] 8.