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5.1.19.1.1 Variation 1: Using Group 1 Organometallics

DOI: 10.1055/sos-SD-005-00119

Spivey, A. C.; Diaper, C. M.Science of Synthesis, (20035129.

Deprotonation of acidic protons using lithium bases is a convenient method for the formation of organolithium reagents, which can subsequently be quenched with halogermanes to give α-amino-, e.g. 13, Scheme 4 [‌5‌] α-isocyano-,[‌34‌] α-imino-,[‌35‌] and α,α-diheteroalkylgermanes,[‌36‌,‌37‌] (the latter functioning as a masked acylgermane Section 5.1.16.4).[‌38‌] α-Alkoxyalkylgermanes 14 have been prepared from the corresponding α-alkoxyalkylstannanes via transmetalation using butyllithium,[‌39‌] whereas monolithiumhalogen exchange or deprotonation has also been carried out using gem-dihalo and trihalo derivatives to give monohaloalkylgermanes and α,α-dihaloalkylgermanes respectively (such as 15 and 16 in Scheme 4). α-Halogermanes can be subsequently converted into the corresponding iodozincs,[‌40‌] which are known to be useful intermediates in organic synthesis.[‌41‌] Attempts to synthesize 1,1-dihaloallylgermanes using this methodology, however, are unsuccessful.[‌42‌]

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