Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A new route to β,gamma;-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcyclopentadiene to provide β,γ-unsaturated ketones. The removal would proceed via a retro-carbonyl-ene process. Synthesis of an alkyl allyl ketone is also described.

Original languageEnglish
Pages (from-to)167-169
Number of pages3
JournalSynlett
Issue number1
DOIs
Publication statusPublished - Jan 4 2007
Externally publishedYes

Fingerprint

Allylation
Ketones
Alcohols
Toluene
Boiling liquids
Heating

Keywords

  • Allylation
  • Cleavage
  • Ketones
  • Pentamethylcyclopentadiene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene. / Iwasaki, Masayuki; Morita, Eiji; Uemura, Minoru; Yorimitsu, Hideki; Oshima, Koichiro.

In: Synlett, No. 1, 04.01.2007, p. 167-169.

Research output: Contribution to journalArticle

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AU - Yorimitsu, Hideki

AU - Oshima, Koichiro

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