Tetrahedron letters

Aliphatic organolithiums by fluorine–lithium exchange: n-octyllithium

M Yus, RP Herrera, A Guijarro

Index: Yus, Miguel; Herrera, Raquel P.; Guijarro, Albert Tetrahedron Letters, 2003 , vol. 44, # 27 p. 5025 - 5027

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Citation Number: 30

Abstract

The reaction of 1-fluorooctane (1) with an excess of lithium powder (4–10 equiv.) and DTBB (2–4 equiv.) in THP at 0° C for 5 min gives a solution of the corresponding 1-octyllithium (2), which reacts then with different electrophiles at 0° C (D2O, MeSiCl, ButCHO, Et2CO), or− 78° C [ClCO2Me,(PhCH2S) 2] or− 40° C (CO2) to room temperature to give, after hydrolysis, the expected products (3). The same process applied to 2-fluorooctane gives mainly ...

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