General and efficient method for the synthesis of alkoxymethylsilanes

Seiji Suga, Keiko Miyamoto, Mitsuru Watanabe, Jun Ichi Yoshida

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Although alkoxymethylsilanes serve as useful building blocks, various efforts to synthesize them by substitution reaction with an alkoxide ion at the carbon adjacent to the silicon failed. To solve this synthetic problem a new route which is very simple to perform was developed. Bromination of (methoxymethyl)trimethylsilane by using N-bromosuccinimide/2,2′-azobisisobutyronitrile (NBS/AIBN) was followed by a substitution by alcohols in the presence of triethylamine to give the corresponding [alkoxy-(methoxy)methyl]trimethylsilanes. These acetals can be used directly for the next reduction with di-isobutylaluminium hydride (DIBAL-H) or Et3SiH/BF3·OEt2 to give alkoxymethylsilanes in good to moderate yields. The success of the substitution reaction with the alcohols suggests that the mechanism is of somewhat SN1 by nature and formation of the cationic intermediate seems to release the steric hindrance around the carbon, allowing the attack of alcohols.

Original languageEnglish
Pages (from-to)469-474
Number of pages6
JournalApplied Organometallic Chemistry
Volume13
Issue number6
Publication statusPublished - 1999
Externally publishedYes

Fingerprint

Substitution reactions
Alcohols
Carbon
Bromosuccinimide
Acetals
Silicon
Hydrides
Ions
triethylamine
azobis(isobutyronitrile)
alkoxyl radical

Keywords

  • Acetal
  • Alkoxymethylsilanes
  • Bromination
  • Electro-organic synthesis
  • Reduction

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Inorganic Chemistry

Cite this

Suga, S., Miyamoto, K., Watanabe, M., & Yoshida, J. I. (1999). General and efficient method for the synthesis of alkoxymethylsilanes. Applied Organometallic Chemistry, 13(6), 469-474.

General and efficient method for the synthesis of alkoxymethylsilanes. / Suga, Seiji; Miyamoto, Keiko; Watanabe, Mitsuru; Yoshida, Jun Ichi.

In: Applied Organometallic Chemistry, Vol. 13, No. 6, 1999, p. 469-474.

Research output: Contribution to journalArticle

Suga, S, Miyamoto, K, Watanabe, M & Yoshida, JI 1999, 'General and efficient method for the synthesis of alkoxymethylsilanes', Applied Organometallic Chemistry, vol. 13, no. 6, pp. 469-474.
Suga, Seiji ; Miyamoto, Keiko ; Watanabe, Mitsuru ; Yoshida, Jun Ichi. / General and efficient method for the synthesis of alkoxymethylsilanes. In: Applied Organometallic Chemistry. 1999 ; Vol. 13, No. 6. pp. 469-474.
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