Description:
AbstractThe synthesis of a compound with a gallium‐carbon double bond, a gallene, was targeted. A series of organogallium compounds stabilized by an N‐heterocyclic carbene, 1,3‐diisopropyl‐4,5‐dimethyl‐imidazol‐2‐ylidene (MeIiPr) or 4‐dimethylaminopyridine (DMAP) was synthesized from Li[GaCl2FlMes] (1; Mes=2,4,6‐trimethylphenyl, Fl=fluorenyl), including MeIiPr→GaClFlMes (3) and DMAP→GaClFlMes (4) and their triflate (7, 9, respectively) and fluoride (8, 10, respectively) derivatives through pseudohalide exchange or nucleophilic substitution at the gallium centre. Treatment of 8 with tBuLi followed by the addition of tolualdehyde gave 11, a 1‐galla‐2,6‐dioxacyclohexane which can reasonably be formed by the sequential addition of two equivalents of the aldehyde to a transient gallene, a compound containing a Ga−C double bond.