Photolysis of 2-alkoxy-. DELTA. 3-1, 3, 4-oxadiazolines. A new route to diazoalkanes

…, M Bekhazi, I Tse-Sheepy, J Warkentin

Index: Majchrzak, Michael W.; Bekhazi, Michel; Tse-Sheepy, Irene; Warkentin, John Journal of Organic Chemistry, 1989 , vol. 54, # 8 p. 1842 - 1845

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Citation Number: 40

Abstract

2-Alkoxy-2, 5, 5-trialkyl-A3-1, 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 ll), which can in turn be photolyzed to the corresponding cyclopropenes (8) and cyclopropanes (12), respectively.