Photochemistry of alkyl halides. 8. Formation of a bridgehead alkene

PJ Kropp, PR Worsham, RI Davidson…

Index: Kropp, Paul J.; Worsham, Paul R.; Davidson, Robert I.; Jones, Tappey H. Journal of the American Chemical Society, 1982 , vol. 104, # 14 p. 3972 - 3980

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Citation Number: 21

Abstract

Abstract: Irradiation of the bridgehead iodides 4, 7, and 10 afforded principally the ionic products 6, 9, and 12 accompanied by small amounts of the reduction products 5, 8, and 11. Studies in methanol-d indicated an absence of pathways leading to ethers 6, 9, and 12 involving bridgehead alkene or propellane intermediates. By contrast, the iodo ether 16 afforded not only the epimeric endo iodide 17, the reduction product 19, and the expected ...