C-, N- and C,N-organostannyl tetrazoles: synthesis, characterisation and reactivity

Abstract

Open-chain C,N-organostannyl tetrazoles, R₂R′Sn(CH₂)_nCN₄SnBu₃(n= 2 or 3, R₂R′= Ph₃; n= 2, R₂R′= Bu₂Ph), have been synthesised by a [3 + 2] cycloaddition reaction between R₃Sn(CH₂)_nCN and SnBu₃(N₃). Prolonged heating of the reaction mixture yields the novel bicyclic species C,N-R₂Sn(CH₂)_nCN₄(n= 2 or 3, R = Ph; n= 2, R = Bu). The reaction chemistry of both classes of compound has been studied, along with a reinvestigation of the parent 5-organo(N-triorganostannyl)tetrazoles RCN₄SnR′₃, by ¹³C and ¹¹⁹Sn NMR spectroscopy. The crystal structure of 2,2-diphenyl-1,7,8,9-tetraaza-2-stannabicyclo[4.3.0]nona-6,8-diene has also been determined.