A New Practical Synthesis of Germylalkoxydienes, Acylgermanes and Ethynylgermanes from α,β-Unsaturated and α-Phenyl Acetals

Sara Allasia; Annamaria Deagostino; Cristina Prandi; Chiara Zavattaro; Paolo Venturello

doi:10.1055/s-2005-918414

PAPER

A New Practical Synthesis of Germylalkoxydienes, Acylgermanes and Ethynylgermanes from α,β-Unsaturated and α-Phenyl Acetals

Sara Allasia, Annamaria Deagostino*, Cristina Prandi, Chiara Zavattaro, Paolo Venturello*
Dipartimento di Chimica Generale ed Organica Applicata dell’Università, Via Pietro Giuria 7, 10125 Torino, Italy
Fax: +39(011)2367646; e-Mail: paolo.venturello@unito.it;

Abstract

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Abstract

The treatment of α,β-unsaturated acetals 1a-f with LIC-KOR base (equimolar mixture of n-BuLi and tert-BuOK) produces α-metalated alkoxy-1,3-dienes that easily react with halotrialkyl- and halotriarylgermanes producing substituted (Z)-alkoxyvinylgermanes 2a-i in good yields. Functionalized dienyl derivatives can be transformed into the corresponding acylgermanes 3a-d under mild acidic hydrolytic conditions. Furthermore, the lithium-potassium mixed reagent promotes the conversion of the α-phenyl acetal 4 into trimethyl(2-phenylethynyl)germane (5).

Key words

acetals - organometallic reagents - superbases - germyldienes - acylgermanes

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