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

Abstract

Reaction of the [1-(4-H 2N–C 6H 4)- closo-1-CB 9H 9] − anion 1 with Me 2CHCH 2CH 2ONO and dilute HCl gives neutral [1-(4-N 2–C 6H 4)- closo-1-CB 9H 9] 3, which reacts with PhNH 2 to form the 19.5 Å [1-{4-(4-H 2N–C 6H 4–NN)–C 6H 4}- closo-1-CB 9H 9] − azo anion 2. Anion 1 with ketones and aldehydes gives imino compounds: with (CH 3) 2CO it gives neutral [1-{4-(Me 2CNH)–C 6H 4}- closo-1-CB 9H 9] 6 and with the para-dialdehyde C 6H 4-1,4-(CHO) 2 it gives the 30.5 Å extended rod-like neutral species [C 6H 4-1,4-{1-(CHNH–C 6H 4)- closo-1-CB 9H 9} 2] 8.