Publication

The preparation of pure allyl- and benzyl-type organoalkali intermediates via organotin compounds

Manfred Schlosser
1991
Journal Articles

Abstract

Superbase metalation of alkenes or alkylbenzenes and subsequent condensation with trialkylstannyl chloride affords allyl- or benzyl-type organotin compds. that can be isolated in pure form. Treatment with sol. reagents such as methyllithium, trimethylsilylmethylpotassium and trimethylsilylmethylcesium generates the corresponding organoalkali derivs., almost quant. and in high purity, suitable for kinetic or spectroscopic studies. E.g., treating Me3SiC(:CH2)Me with KOCMe3 and BuLi in THF and then with Me3SnCl gave 45% CH2:C(SiMe3)CH2SnMe3, which when treated with Me3SiCH2Cs gave 95% of the Cs deriv. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/4a48f171-7412-45bf-84da-46dbcca78738

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Manfred Schlosser
1991
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/4a48f171-7412-45bf-84da-46dbcca78738

About this result

Related concepts (16)

Organotin chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin carbon bonds. The first organotin compound was diethyltin diiodide (), discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

Organogermanium chemistry

Organogermanium chemistry is the science of chemical species containing one or more C–Ge bonds. Germanium shares group 14 in the periodic table with carbon, silicon, tin and lead. Historically, organogermanes are considered as nucleophiles and the reactivity of them is between that of organosilicon and organotin compounds. Some organogermanes have enhanced reactivity compared with their organosilicon and organoboron analogues in some cross-coupling reactions.

Organometallic chemistry

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well.