Synthesis of β,γ-unsaturated ketones from acid chlorides through carbon-pentamethylcyclopentadienyl bond formation and cleavage

Minoru Uemura, Masayuki Iwasaki, Eiji Morita, Hideki Yorimitsu, Koichiro Oshima

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of acid chlorides with lithium pentamethylcyclopentadienide afforded the corresponding pentamethyl-cyclopentadienyl ketones in high yield. These ketones were treated with an allylaluminum reagent to form the corresponding 3-butenyl alcohols. Removal of pentamethylcyclopentadiene upon heating or treatment with a catalytic amount of trichloroacetic acid yielded the corresponding β,γ-unsaturated ketones in good yields.

Original languageEnglish
Pages (from-to)2400-2405
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume80
Issue number12
DOIs
Publication statusPublished - 2007
Externally publishedYes

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Ketones
Chlorides
Carbon
Acids
Trichloroacetic Acid
Lithium
Alcohols
Heating

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of β,γ-unsaturated ketones from acid chlorides through carbon-pentamethylcyclopentadienyl bond formation and cleavage. / Uemura, Minoru; Iwasaki, Masayuki; Morita, Eiji; Yorimitsu, Hideki; Oshima, Koichiro.

In: Bulletin of the Chemical Society of Japan, Vol. 80, No. 12, 2007, p. 2400-2405.

Research output: Contribution to journalArticle

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AU - Oshima, Koichiro

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