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Addition of Aldehydes to Germenes: The Influence of Solvent

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posted on 13.06.2011, 00:00 by Christopher J. Allan, Crispin R. W. Reinhold, Laura C. Pavelka, Kim M. Baines
The addition of trans-(2-phenylcyclopropyl)carboxaldehyde to dimesitylfluorenylidenegermane produced four diastereomers of a 1,2-oxagermin, 7ad, 2,2,4,4-tetramesityl-1,3-dioxadigermetane (8), and fluorenylidene(trans-2-phenylcyclopropyl)methane (9). The ratio of the products showed a strong dependence on the solvent: 7ad were formed almost exclusively when ether or benzene was used as the solvent for the reaction, whereas 1,3-dioxadigermetane 8 and alkene 9 were the major products formed in THF. A mechanism is proposed to account for the observations.