- Novel Transformations of 1,2-Dioxetanes: β-Hydroxy Ethers by Addition of Alkyllithium Reagents
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The reaction of 1,2-dioxetanes with alkyllithium reagents was investigated.The 3,3-disubstituted dioxetanes 2a,d and their halogen-substituted analogues 2b,c, which were used as probes to differentiate between the mechanistic alternatives (SN2 reactivity vs. single-electron transfer), reacted with n-BuLi to afford the β-hydroxy ethers 3a-d.Additionally, the epoxide 4 was obtained from dioxetanes 2b,c.The epoxide 5 and a small amount of acetophenone were found in the reaction of dioxetane 2c with triphenylmethyllithium, but only the minor part of the dioxetane-derived products could be identified.The observation of the epoxides 4 and 5 led to the mechanistic conclusion that nucleophilic attack (SN2 reactivity) is the most prominent process in this reaction.Key Words: Dioxetanes / Single electron transfer vs. nucleophilic attack / Ethers, β-hydroxy / Alkyllithium reagents
- Adam, Waldemar,Heil, Markus
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p. 235 - 241
(2007/10/02)
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