89358-16-7Relevant academic research and scientific papers
β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds
Barluenga, Jose,Florez, Josefa,Yus, Miguel
, p. 3019 - 3026 (2007/10/02)
The reaction of different chlorohydrins with n-butyl-lithium at -78 deg C followed by metallation wiht lithium naphthalenide at the same temperature leads to very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to metal.The reaction of these intermediates with several electriphiles leads to mono- as well as bi-functionalized organic compounds.Thus, treatment of these dianions with deuterium oxide, oxygen, carbon dioxide, benzyl bromide, dimethyl disulphide, and carbonyl compounds, gave 2-deuterioalcohols, 1,2-diols, β-hydroxy-acids, 2-benzyl alcohols, 2-hydroxy-thioethers, and 1,3-diols respectively.The preparation of β-substituted organolithium derivatives can be alternatively carried out starting from α-chloroketones by the same procedure.When the lithium atom is linked to a secondary carbon atom the dianions are very unstable and decompose, even at -100 deg C, by β-elimination yielding the corresponding olefins.
