Silyl–substituted germenes. The reactions of germenes generated thermally from acyltris(trimethylsilyl)germane with conjugated enones

Naka, Akinobu; Ueda, Shinsuke; Fujimoto, Hiroki; Miura, Tohru; Kobayashi, Hisayoshi; Ishikawa, Mitsuo

doi:10.1016/j.jorganchem.2010.04.007

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“…Herein, we now report on the addition of probe 2 to a stable germene to investigate the mechanism of this important reaction. − Two naturally polarized germenes were considered as substrates for this study: 1,1-dimesitylneopentylgermene ( 3 ) and dimesitylfluorenylidenegermane ( 4 ) . Both germenes are stable in solution and can be readily synthesized.…”

Section: Introductionmentioning

confidence: 99%

Addition of Aldehydes to Germenes: The Influence of Solvent

Allan¹,

Reinhold²,

Pavelka³

et al. 2011

Organometallics

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The addition of trans-(2-phenylcyclopropyl)carboxaldehyde to dimesitylfluorenylidenegermane produced four diastereomers of a 1,2-oxagermin, 7aÀd, 2,2,4,4tetramesityl-1,3-dioxadigermetane ( 8), and fluorenylidene-(trans-2-phenylcyclopropyl)methane ( 9). The ratio of the products showed a strong dependence on the solvent: 7aÀd 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.

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