Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides
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1979
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By decomposition of alkyl hydroperoxides 1-8 with ferrous sulfate-cupric acetate reagent, intramolecular functionalisation of remote non-activated C atom takes place and unsaturated alcohols with double bond mainly at δ-position are obtained. The reaction proceeds involving the corresponding alkoxy radical 9 and δ-carbon radical 10 as intermediates. One-electron oxidative interception of δ-carbon radical by cupric acetate does not involve the corresponding carbonium ion; instead, the alkyl-copper intermediate 11 is formed and by elimination affords olefinic alcohols. The isotope effect for this elimination process was found to be kh/kd=6.1. © 1979.
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Tetrahedron, 1979, 35, 17, 2021-2026Publisher:
- Pergamon Press
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IHTMTY - JOUR AU - Čeković, Živorad AU - Dimitrijević, Lj. AU - Djokić, G AU - Srnić, T PY - 1979 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2752 AB - By decomposition of alkyl hydroperoxides 1-8 with ferrous sulfate-cupric acetate reagent, intramolecular functionalisation of remote non-activated C atom takes place and unsaturated alcohols with double bond mainly at δ-position are obtained. The reaction proceeds involving the corresponding alkoxy radical 9 and δ-carbon radical 10 as intermediates. One-electron oxidative interception of δ-carbon radical by cupric acetate does not involve the corresponding carbonium ion; instead, the alkyl-copper intermediate 11 is formed and by elimination affords olefinic alcohols. The isotope effect for this elimination process was found to be kh/kd=6.1. © 1979. PB - Pergamon Press T2 - Tetrahedron T2 - Tetrahedron T1 - Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides VL - 35 IS - 17 SP - 2021 EP - 2026 DO - 10.1016/S0040-4020(01)88972-9 ER -
@article{ author = "Čeković, Živorad and Dimitrijević, Lj. and Djokić, G and Srnić, T", year = "1979", abstract = "By decomposition of alkyl hydroperoxides 1-8 with ferrous sulfate-cupric acetate reagent, intramolecular functionalisation of remote non-activated C atom takes place and unsaturated alcohols with double bond mainly at δ-position are obtained. The reaction proceeds involving the corresponding alkoxy radical 9 and δ-carbon radical 10 as intermediates. One-electron oxidative interception of δ-carbon radical by cupric acetate does not involve the corresponding carbonium ion; instead, the alkyl-copper intermediate 11 is formed and by elimination affords olefinic alcohols. The isotope effect for this elimination process was found to be kh/kd=6.1. © 1979.", publisher = "Pergamon Press", journal = "Tetrahedron, Tetrahedron", title = "Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides", volume = "35", number = "17", pages = "2021-2026", doi = "10.1016/S0040-4020(01)88972-9" }
Čeković, Ž., Dimitrijević, Lj., Djokić, G.,& Srnić, T.. (1979). Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides. in Tetrahedron Pergamon Press., 35(17), 2021-2026. https://doi.org/10.1016/S0040-4020(01)88972-9
Čeković Ž, Dimitrijević L, Djokić G, Srnić T. Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides. in Tetrahedron. 1979;35(17):2021-2026. doi:10.1016/S0040-4020(01)88972-9 .
Čeković, Živorad, Dimitrijević, Lj., Djokić, G, Srnić, T, "Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides" in Tetrahedron, 35, no. 17 (1979):2021-2026, https://doi.org/10.1016/S0040-4020(01)88972-9 . .