A facile preparation and cyclopropanation of 1-alkenylsilanols

Kazunori Hirabayashi, Eisuke Takahisa, Yasushi Nishihara, Atsunori Mori, Tamejiro Hiyama

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Alkenylsilanols are prepared by the reaction of hexamethyltrisiloxane (D 3) with alkenyllithiums or alternatively by the reaction of cyclic siloxanes substituted by an alkenyl group with organolithiums and transformed to the corresponding cyclopropylsilanols using diiodomethane and diethylzinc. Lithium alkenylsilanolates, primary products of the preparation, also undergo cyclopropanation. As in the case of allylic alcohols, the silanol functionality is found to enhance the rate of cyclopropanation compared with that of alkenyltrialkylsilane or alkoxydialkylsilane. The obtained cyclopropylsilanols are further converted into the corresponding cyclopropanols by the Tamao oxidation.

Original languageEnglish
Pages (from-to)2409-2417
Number of pages9
JournalBulletin of the Chemical Society of Japan
Volume71
Issue number10
Publication statusPublished - 1998
Externally publishedYes

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Siloxanes
Lithium
Oxidation
diethylzinc
allyl alcohol
silanol
cyclopropanol
methylene iodide

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Hirabayashi, K., Takahisa, E., Nishihara, Y., Mori, A., & Hiyama, T. (1998). A facile preparation and cyclopropanation of 1-alkenylsilanols. Bulletin of the Chemical Society of Japan, 71(10), 2409-2417.

A facile preparation and cyclopropanation of 1-alkenylsilanols. / Hirabayashi, Kazunori; Takahisa, Eisuke; Nishihara, Yasushi; Mori, Atsunori; Hiyama, Tamejiro.

In: Bulletin of the Chemical Society of Japan, Vol. 71, No. 10, 1998, p. 2409-2417.

Research output: Contribution to journalArticle

Hirabayashi, K, Takahisa, E, Nishihara, Y, Mori, A & Hiyama, T 1998, 'A facile preparation and cyclopropanation of 1-alkenylsilanols', Bulletin of the Chemical Society of Japan, vol. 71, no. 10, pp. 2409-2417.
Hirabayashi, Kazunori ; Takahisa, Eisuke ; Nishihara, Yasushi ; Mori, Atsunori ; Hiyama, Tamejiro. / A facile preparation and cyclopropanation of 1-alkenylsilanols. In: Bulletin of the Chemical Society of Japan. 1998 ; Vol. 71, No. 10. pp. 2409-2417.
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