Polygermoxanes suitable for biochemical purposes. Part I. Digermoxanes (low‐viscosity oils)

Duverneuil, G; Mazerolles, P.; Perrier, Elisabeth

doi:10.1002/aoc.590080207

Cited by 11 publications

(1 citation statement)

References 30 publications

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“…To the best of our knowledge, only five have been structurally described: (2,6-Mes 2 C 6 H 3 ) 2 Ge(OH) 2 , [13] tBu 2 -Ge(OH) 2 , [20,21] [(Me 3 Si) 2 N] 2 Ge(OH) 2 , [22] HN(CH 2 CH 2 O) 2 -Ge(OH) 2 , [23] (tpp)Ge(OH) 2 (tpp = meso-tetraphenylporphyrinato); [24] some others, that is, Mes 2 Ge(OH) 2 , [25] (2,6-Me 2 C 6 H 3 ) 2 Ge(OH) 2 , [26] (C 6 Cl 5 ) 2 Ge(OH) 2 [27] and tbt(tip)-Ge(OH) 2 [9] have been characterized by usual spectroscopic methods.…”

Section: Introductionmentioning

confidence: 99%

A Synthetic Equivalent of a Germanone Derivative

et al. 2008

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Reaction of two molar equivalents of 2,6‐bis(diisopropylaminomethyl)phenyllithium (ArLi) with tetramethoxygermane afforded the colourless crystalline dimethoxy bis[2,6‐bis(diisopropylaminomethyl)phenyl]germane Ar2Ge(OMe)2 (1) in good yield. Treatment of 1 with AgF/H2O led to the fluorohydroxy derivative Ar2Ge(F)OH (2), which was characterized, among other techniques, by single‐crystal structure analysis. The corresponding lithio compound Ar2Ge(F)OLi (3) obtained from 2 by reaction with tBuLi behaves as a synthetic equivalent of the heavier analogue of ketone[Ar2Ge=O, 5]. Germanone 5 could not be isolated even at low temperature due to the impossibility of dissociating it from LiF. Treatment of 3 with various reactants on the basis of the known reactivity of ketones led to the expected products. The reaction of 3 with H2O led, as expected, quantitatively to the germanium gem‐diol Ar2Ge(OH)2 (6) as colourless crystals. Such gem‐diols are scarce compounds and only a few are structurally known; in our case, 6 is stabilized by a hydrogen linkage between the hydrogen atoms of the alcohol functionalities and the nitrogen atoms. Other trapping reactions of 3 were investigated with tBuLi and methanol, and the corresponding germanols Ar2Ge(tBu)OH (7) and Ar2Ge(OMe)OH (8) were isolated after hydrolysis in good yields. Attempts to eliminate LiF from 3 by using the chelating agent 1,4,7,10‐tetraoxacyclododecane (12‐crown‐4) allowed us to isolate lithio complex 9. Generation of germanones from fluorohydroxygermanes and their lithio derivatives appears to be a new promising method. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Introductionmentioning

confidence: 99%

A Synthetic Equivalent of a Germanone Derivative

et al. 2008

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Synthesis and bioactivities of novel organogermanium sesquioxides containing?-aminophosphonate groups

et al. 1999

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In order to search for novel antitumor drugs with high activity and low toxicity, a series of novel organogermanium sesquioxides containing α‐aminophosphonate groups were synthesized by the hydrolysis of O,O‐diphenyl N‐trichlorogermylpropiono‐α‐aminophosphonates. Their structures were confirmed by 1H NMR, 31P NMR, and IR spectroscopy and by elemental analysis. Data of 1H NMR and IR spectroscopy indicated that the title compounds are polymeric organogermanium sesquioxides. The results of bioassay showed that the products possess potential anticancer activities. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 209–212, 1999

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Polygermoxanes suitable for biochemical purposes: II Linear trigermoxanes (high‐viscosity oils)

Duverneuil

Mazerolles

Perrier³

1995

Applied Organom Chemis

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Linear trigermoxanes, R'R:GeOGe(R3),0GeR:R', a new series of organogermanium compounds, were synthesized by reaction of a lithium organogermanolate with a suitable organogermanium dihalide. With alkyl or phenyl substituents, these trigermoxanes are structurally unstable viscous oils, due to redistribution reactions. When R3 substituents are bulky groups, such as mesityl, trigermoxanes are thermally and structurally stable oils; depending on the R' and R2 substituents their viscosities lie in the range 240 to more than 1500 cPo (mPa s) at 20 "C. When both terminal germanium atoms are substituted with two mesityl groups, trigermoxanes are stable glassy solids.

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Polygermoxanes suitable for biochemical purposes. Part I. Digermoxanes (low‐viscosity oils)

Cited by 11 publications

References 30 publications

A Synthetic Equivalent of a Germanone Derivative

A Synthetic Equivalent of a Germanone Derivative

Synthesis and bioactivities of novel organogermanium sesquioxides containing?-aminophosphonate groups

Polygermoxanes suitable for biochemical purposes: II Linear trigermoxanes (high‐viscosity oils)

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