Reactions of (CO)5MnSi(CH3)3 with .alpha.-bromo carbonyl and related organic compounds. Facile reductive silylation Academic Article uri icon

abstract

  • Reactions of (CO)6MnSi(CH3)3 (1, 1.0-3.0 equiv, 25–50 °C) with α-bromo carbonyl compounds, α-(diphenylphosphino)isobutyraldehyde, and α-bromo dimethyl acetals and ketals are examined. The α-bromo carbonyl compounds are reductively silylated to trimethylsilyl enol ethers in fair to excellent yields. The initial inorganic product is (CO)6MnBr. A mechanism is proposed in which 1 initially silylates the carbonyl oxygen and (CO)5Mn- subsequently abstracts bromine. The phosphino aldehyde is similarly reduced, and the acetals and ketals are converted to methyl enol ethers and CH3OSi(CH3)3. The synthetic utility of these transformations is discussed. © 1985, American Chemical Society. All rights reserved.

author list (cited authors)

  • Marsi, M., Brinkman, K. C., Lisensky, C. A., Vaughn, G. D., & Gladysz, J. A.

citation count

  • 6

publication date

  • September 1985