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(Acetoxymethyl)methylphenylgermane [PhMeGe(H)CH 2 OAc, lc] was synthesized by a five-step synthesis starting from trichloro(chloromethyl)germane [Cl 3 GeCH 2 Cl → PhCl 2 GeCH 2 Cl → PhMeGe(Cl)CH 2 Cl → PhMeGe(OAc)CH 2 OAc → PhMeGe(H)CH 2 OH → PhMeGe(H)CH 2 OAc]. The germane le and its carbon analogue PhMeC(H)CH 2 OAc (la) are thermally stable (solutions in C 6 D 6 ; 160 °C, 48 h), whereas the structurally analogous silane PhMeSi(H)CH 2 OAc (lb) undergoes a rearrangement upon heating (formation of the silane PhMe 2 SiOAc; half-life in C 6 D 6  at 135 °C: 7.7 h). By analogy to the perfume la (hydratropyl acetate) and its silicon analogue lb (sila-hydratropyl acetate), the germane lc (germa-hydra-tropyl acetate) exhibits a sweet-floral odor. Despite of some differences, the olfactoric properties of the C/Si/Ge-analogues la/lb/lc are mainly characterized by analogies.

zeitschrift für naturforschung b

(Acetoxymethyl)methylphenylgerman: Synthese, thermisches Verhalten und olfaktorische Eigenschaften / (Acetoxymethyl)methylphenylgermane: Synthesis, Thermal Behaviour and Olfactoric Properties