Si- and C-Functional Organosilicon Building Blocks for Synthesis Based on 4-Silacyclohexan-1-ones Containing the Silicon Protecting Groups MOP (4-Methoxyphenyl), DMOP (2,6-Dimethoxyphenyl), or TMOP (2,4,6-Trimethoxyphenyl).
4-Silacyclohexan-1-ones 1a-1c, 4-silacyclohexan-1-one oximes 2a-2c, 1,4-azasilepan-7-ones 3a-3c, 1,4-azasilepanes 4a-4c, and 2-bromo-4-silacyclohexan-1-ones 5a and 5b were prepared in multistep syntheses, starting from trimethoxypropylsilane. All of these compounds represent C-functional (R2C═O, R2C═N-OH, R-NH(C═O)-R, R2NH, or R3C-Br) silicon-containing heterocycles that contain Si-MOP, Si-DMOP, or Si-TMOP moieties (MOP = 4-methoxyphenyl; DMOP = 2,6-dimethoxyphenyl; TMOP = 2,4,6-trimethoxyphenyl), which can be cleaved under mild conditions by protodesilylation. As a proof of principle, compounds 3a-3c were transformed quantitatively and selectively into the chlorosilane 6 (treatment with hydrogen chloride in dichloromethane). Thus, the C- and Si-functional compounds 1a-1c, 2a-2c, 3a-3c, 4a-4c, 5a, and 5b represent versatile building blocks for synthesis.
†Institut für Anorganische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Marcel
M
Geyer
Olle
O
Karlsson
†Institut für Anorganische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Johannes A
JA
Baus
Eric
E
Wellner
†Institut für Anorganische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Reinhold
R
Tacke
D001555:Benzene Derivatives / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*
D001555:Benzene Derivatives; D017646:Organosilicon Compounds; D010091:Oximes; D002244:Carbon; D012825:Silicon