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- W2738471008 abstract "Sodium diisopropylamide in tetrahydrofuran is an effective base for the metalation of 1,4-dienes and isomerization of alkenes. Dienes metalate via tetrasolvated sodium amide monomers, whereas 1-pentene is isomerized by trisolvated monomers. Facile, highly Z-selective isomerizations are observed for allyl ethers under conditions that compare favorably to those of existing protocols. The selectivity is independent of the substituents on the allyl ethers; rate and computational data show that the rates, mechanisms, and roles of sodium-oxygen contacts are substituent-dependent. The competing influences of substrate coordination and solvent coordination to sodium are discussed." @default.
- W2738471008 created "2017-07-31" @default.
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- W2738471008 date "2017-08-14" @default.
- W2738471008 modified "2023-10-03" @default.
- W2738471008 title "Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Alkene Isomerizations and Diene Metalations" @default.
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- W2738471008 doi "https://doi.org/10.1021/jacs.7b05218" @default.
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