Photolysis of 2-Alkoxy-Δ3-1,3,4-oxadiazolines. A New Route to Diazoalkanes

Article abstract of DOI:10.1021/jo00269a019

2-Alkoxy-2,5,5-trialkyl-Δ³-1,3,4-oxadiazolines (2), when photolyzed in solution with 300-nm light, afford the appropriate diazoalkane (3) and ester (4) in high yield.The diazoalkanes undergo intermolecular reaction, giving rise to azines (5), or they can be trapped in situ with 1,3-dipolarophiles to afford cycloadducts (7 or 11), which can in turn be photolyzed to the corresponding cyclopropenes (8) and cyclopropanes (12), respectively.