Development of Practical Method for Fixation of Nitric Oxide

Abstract

Nitric oxide is stable paramagnetic gas, is considered as air-pollutant, and is also known to play fundamental role in biochemical processes. While a number of approaches to fix nitric oxide into organic molecules have been investigated for one and half centuries, yields of nitrogen containing products and reproducibility of the reaction were usually low to moderate. We solved these problems and reported herein a practical method to fix nitric oxide into organic molecules. A key feature of the reaction was use of alkynyllithium as substrate. Reaction of nitric oxide with alkynyllithiums cleanly proceeded for a short period to produce 5-substituted 1,2,3-oxadiazole 3-oxides in good yields after quenching with water. When deuterium oxide and chlorotrimethylsilane were used as quenching agent, 4-deuteriated and silylated products were produced, respectively.