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

Abstract

(Acetoxymethyl)methylphenylgermane [PhMeGe(H)CH2OAc, lc] was synthesized by a five-step synthesis starting from trichloro(chloromethyl)germane [Cl3GeCH2Cl → PhCl2GeCH2Cl → PhMeGe(Cl)CH2Cl → PhMeGe(OAc)CH2OAc → PhMeGe(H)CH2OH → PhMeGe(H)CH2OAc]. The germane le and its carbon analogue PhMeC(H)CH2OAc (la) are thermally stable (solutions in C6D6; 160 °C, 48 h), whereas the structurally analogous silane PhMeSi(H)CH2OAc (lb) undergoes a rearrangement upon heating (formation of the silane PhMe2SiOAc; half-life in C6D6 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.