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Naked Fluoride Ion Sources:  Synthesis, Characterization, and Coupling Reaction of 1-Methylhexamethylenetetramine Fluoride

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journal contribution
posted on 08.01.1997, 00:00 by Robert Z. Gnann, Ross I. Wagner, Karl O. Christe, Robert Bau, George A. Olah, Wiliam W. Wilson
Anhydrous 1-methylhexamethylenetetramine (also referred to as N-methylurotropinium or methylhexaminium) fluoride was prepared by either halogen exchange between the corresponding iodide and AgF or by a single-step, one-pot, self-assembling synthesis from aqueous CH3NH2, HF, formaldehyde, and NH3. It was characterized by NMR and vibrational spectroscopy. Its hydrate undergoes at 70 °C a Sommelet-type ring opening and coupling reaction to form a potential cryptand system consisting of two bicyclic triazine groups that are connected through a methylene bridge and contain eight ternary nitrogen atoms. The compound was characterized by multinuclear NMR and vibrational spectroscopy, and its structure was determined from single-crystal X-ray diffraction data.