Volume 31, Issue 51
Organoelement Compounds
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ChemInform Abstract: Trialkylmanganate Mediated Radical Addition of Triphenylgermane to Carbon—Carbon Multiple Bonds.

Hidenori Kinoshita

Hidenori Kinoshita

Dep. Mater. Chem., Grad. Sch. Eng., Kyoto Univ., Sakyo, Kyoto 606, Japan

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Hirotada Kakiya

Hirotada Kakiya

Dep. Mater. Chem., Grad. Sch. Eng., Kyoto Univ., Sakyo, Kyoto 606, Japan

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Koichiro Oshima

Koichiro Oshima

Dep. Mater. Chem., Grad. Sch. Eng., Kyoto Univ., Sakyo, Kyoto 606, Japan

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First published: 31 May 2010

Abstract

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ChemInform Abstract

The addition of triphenylgermane to carbon—carbon multiple bonds via the corresponding manganese ate complex, tris(triphenylgermyl)manganate (II) or via a catalytic pathway using tributylmanganate is investigated. The stereochemical outcome of the former reaction depends on the molar ratio between the manganese reagent and the acetylenic compound. An excess of the reagent produces exclusively the corresponding E-alkene (III) whereas the Z-isomer (IV) becomes the main product with excess acetylenic compound. It is assumed that the reaction proceeds in a radical pathway and tributylmanganate(II) is an initiator. Thus, the treatment of C—C multiple bonds with triphenylgermane in the presence of catalytic amounts of tributylmanganate provides the corresponding addition products in high yields.

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