Carbenes and the oxygen-hydrogen bond: bicycloalkylidenes

W Kirmse, T Meinert, DA Modarelli…

Index: Kirmse, Wolfgang; Meinert, Thomas; Modarelli, David A.; Platz, Matthew S. Journal of the American Chemical Society, 1993 , vol. 115, # 20 p. 8918 - 8927

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Citation Number: 44

Abstract

Abstract: Photolyses of spirobicyclic diazirines in alcohols have been investigated in order to elucidate the insertion reactions of bicycloalkylidenes with 0-H bonds. The formation of ethers from norbornane-derived diazirines (16 and 30) was traced to the intervention of diazo compounds which react by way of diazonium ions. Scavenging of the diazo compounds with potent dipolarophiles led to almost exclusive formation of nortricyclenes ...