(Thioacetoxy-S-methyl)diorganylsilane und (Mercaptomethyl)diorganylsilane: Synthese und Eigenschaften

Article abstract of DOI:10.1016/0022-328X(90)85346-Z

The novel synthesis of the (thioacetoxy-S-methyl)diorganylsilanes (CH3)2Si(H)CH2SC(O)CH3 (9) and (C6H5)2Si(H)CH2SC(O)CH3 (10) and the (mercaptomethyl)diorganylsilanes (CH3)2Si(H)CH2SH (11) and (C6H5)2Si(H)CH2SH (12) is described.The silanes 11 and 12 are easy to handle, whereas the structurally analogous (hydroxymethyl)diorganylsilanes (CH3)2Si(H)CH2OH (1) and (C6H5)2Si(H)CH2OH (2) tend to undergo a base-catalyzed decomposition (formation of oligomeric (polymeric) alkoxysilanes and hydrogen).In contrast to the thermally unstable (acetoxymethyl)diorganylsilanes (CH3)2Si(H)CH2OC(O)CH3 (3) and (C6H5)2Si(H)CH2OC(O)CH3 (4) ( -> rearrangement to the corresponding acetoxy(methyl)diorganylsilanes (CH3)3SiOC(O)CH3 (5) and CH3(C6H5)2SiOC(O)CH3 (6)), the thio-analogues 9 and 10 are thermally stable (1 molar solutions in C6D6, 30 h at 180 deg C).