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Regioselective Protonation of Allyllithium CompoundsDedicated to Prof. W. Tochtermann on the occasion of his 60th birthday. (1994)

Lüning, Ulrich ; Wangnick, Carsten ; Kümmerlin, Martin

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 2431-2433

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ISSN: 0009-2940

Keywords: Protonation, regioselective ; Allyllithium compound ; Allyl anion ; General acid ; Regioselectivity ; Aging ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: By varying the general acid, the regioselectivity of the protonation of (triphenylsilyl)allyllithium (1) in diethyl ether in the presence of HMPT can be changed from 9:1 to 1:9 at room temperature. When other aprotic solvents are used, the nature of the lithium salt changes, and the selectivity decreases. The regioselectivity of the protonation of the dithio-stabilized allyllithium 4 by water is highly dependent on the age of the allyllithium solution with α/γ ratios varying from 2.7:1 to 1:3.5.

Additional Material: 3 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19941271214

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