NAKED FLUORIDE-ION SOURCES - SYNTHESIS, CHARACTERIZATION, AND COUPLING REACTION OF L-METHYLHEXAMETHYLENETETRAMINE FLUORIDE

Anhydrous 1-methylhexamethylenetetramine (also referred to as N-methyl urotropinium or methylhexaminium) fluoride was prepared by either halo gen exchange between the corresponding iodide and AgF or by a single-s tep, one-pot, self-assembling synthesis from aqueous CH3NH2, HF, forma ldehyde, and NH3. It was characterized by NMR and vibrational spectros copy. Its hydrate undergoes at 70 degrees C a Sommelet-type ring openi ng and coupling reaction to form a potential cryptand system consistin g of two bicyclic triazine groups that are connected through a methyle ne bridge and contain eight ternary nitrogen atoms. The compound was c haracterized by multinuclear NMR and vibrational spectroscopy, and its structure was determined from single-crystal X-ray diffraction data.