4,5,9,10-Tetrahydro-3H,8H-2a,5a,7a,10a-tetraazadicyclopenta[ef,kl]heptalene

Abstract

[176650-00-3] C12H14N4 (MW 216.28) InChI = 1S/C12H16N4/c1-3-13-7-9-15-5-2-6-16-10-8-14(4-1)12(16)11(13)15/h7-10H,1-6H2 InChIKey = MCACHEZOFYGKBY-UHFFFAOYSA-N (reagent used as a neutral organic electron donor in electron transfer reactions) Physical Data: mp 102–103 °C(decomp).1 Solubility: very soluble in diethyl ether, THF, DMF, DMSO, DCM; soluble in hexane. Form Supplied in: yellow solid. Analysis of Reagent Purity: 1H NMR. Preparative Methods: the reagent is prepared according to eq 1. Dry 1,1′,3,3′-bis(trimethylene)bis(imidazolium) diiodide (10 g) and NaH (6.779 g, 8.0 equiv, 60% dispersion in mineral oil) were placed in a Schlenk flask under argon. The mixture was washed with dry hexane (3 × 80 mL). After removing the residual hexane under vacuum, the system was refilled with argon. Liquid ammonia (150 mL) was condensed into the flask while a steady flow of argon gas was maintained at all times during the course of the reaction. The mixture was stirred at room temperature for 2 h; then the ammonia was allowed to evaporate. The resulting solid was extracted with deoxygenated dry diethyl ether (3 × 80 mL) in a glove box under a nitrogen atmosphere. Evaporation of the extracts gave 4.47 g (98%) of the reagent as a yellow free-flowing solid.2 (1) Handling, Storage, and Precautions: the reagent is stable in a glove box for several months without noticeable decomposition. It should be handled under an inert atmosphere at all times, preferably in a glove box. It is extremely sensitive to oxygen, and to moisture. It is stable in most aprotic solvents, but can exchange protons with acetonitrile. The mixture of this reagent and sodium hydride is pyrophoric.