Steuerung der Reaktion von <i>n</i>‐Butyllithium mit Benzo[<i>b</i>]tellurol durch das Lösungsmittel – wahlweise Metallierung oder Tellur‐Lithium‐Austausch zu einem interessanten Lithiostyryllithium

Maercker, Adalbert; Bodenstedt, Heinrich; Brandsma, L.

doi:10.1002/ange.19921041021

Cited by 18 publications

(2 citation statements)

References 20 publications

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“…As a large group 14 element, tin is able to react with nucleophiles by expanding its coordination sphere to give a pentacoordinate reactive ate complex. Such intermediates have been described before,38, 43 and, in one instance, have even been isolated 43. Lithium stannates typically have lower reactivity towards electrophiles than other organolithium reagents 40.…”

Section: Resultsmentioning

confidence: 88%

High‐Yield Lithiation of Azobenzenes by Tin–Lithium Exchange

Strueben

Lipfert

Springer

et al. 2015

Chemistry A European J

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The lithiation of halogenated azobenzenes by halogen-lithium exchange commonly leads to substantial degradation of the azo group to give hydrazine derivatives besides the desired aryl lithium species. Yields of quenching reactions with electrophiles are therefore low. This work shows that a transmetalation reaction of easily accessible stannylated azobenzenes with methyllithium leads to a near-quantitative lithiation of azobenzenes in para, meta, and ortho positions. To investigate the scope of the reaction, various lithiated azobenzenes were quenched with a variety of electrophiles. Furthermore, mechanistic (119) Sn NMR spectroscopic studies on the formation of lithiated azobenzenes are presented. A tin ate complex of the azobenzene was detected and characterized at low temperature.

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Section: Resultsmentioning

confidence: 88%

High‐Yield Lithiation of Azobenzenes by Tin–Lithium Exchange

Strueben

Lipfert

Springer

et al. 2015

Chemistry A European J

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“…This 1,3-dilithio compound serves as a bifunctional synthetic building block suitable for the preparation of inorganic and organic compounds containing a -CH,-S-CH,-structural unit. The most important strategies for the synthesis of organolithium compounds of general formula R,E-CH,-Li (E = element of group [14][15][16] are as follows: 1) hydrogen-lithium exchange, 2) halogen-lithium exchange, 3) metal-lithium exchange (each with either lithium bases or lithium metal) . ['] Applying these strategies to the preparation of dilithio compounds of the general formula Li-CH,-E-CH,-Li shows that direct metalation (first strategy) is often too slow (e.g., for RP(CH,),)[4J or too unreactive (e.g., for S(CH,),) for preparative purposes.…”

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confidence: 99%