Synthese der Si-funktionellen Acetylsilane tBu(Me$_3$SiCH$_2$)[MeC(O)]SiF und tBu(Me$_3$SiCH$_2$)[MeC(O)]SiH sowie Synthese und Kristallstruktur des Acetylsilanols tBu(Me$_3$SiCH$_2$)[MeC(O)]SiOH: Substrate für mikrobielle Reduktionen

Abstract

The racemic Si-functional acetylsilanes tBu(Me$_3$SiCH$_2$)[ MeC(O)]SiF (1) and tBu(Me$_3$SiCH$_2$)[MeC(O)]SiH (2) and the racemic acetylsilanol tBu(Me$_3$SiCH$_2$)[MeC(O)]SiOH (3) were synthesized from Si(OMe)$_4$ (4) as substrates for microbial reductions [4 -> tBuSi(OMe)$_3$ (5) -> tBu(Me$_3$SiCH$_2$)Si(OMe)$_2$ (6) -> tBu(Me$_3$SiCH$_2$)SiF$_2$ (7)-> tBu(Me$_3$SiCH$_2$)(CH$_2$ = C(OMe))SiF (8) -> 1; 8 -> tBu(Me$_3$SiCH$_2$)[CH$_2$ = C(OMe)]SiH (9) -> 2; 6 -> tBu(Me$_3$SiCH$_2$)[CH$_2$ = C(OMe)]SiOMe (10) -> 3]. Compounds 1-3 were found to be reduced by cells of Trigonapsis variabilis (DSM 70714) ( = SiC(O)Me -> = SiCH(OH)Me}. The crystal and molecular structure of 3 was studied by singlecrystal X-ray diffraction. In the crystal, racemic 3 forms infinite chains built up by intermolecular 0-H .. ·O bonds between the hydroxyl and acetyl groups of molecules of the same absolute configuration