Synthesis of 5-substituted 4,4-disubstituted 2-cyclohexen-1-ones by electro-generated base promoted Michael addition of 4,4-disubstituted 2,5-cyclohexadien-1-ones

Sigeru Torii, Naoya Hayashi, Manabu Kuroboshi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

5-Substituted 4,4-dialkoxy-2-cyclohexen-1-ones were electro-synthesized from 4,4-disubstituted 2,5-cyclohexadien-1-ones, which were obtained from 1,4-dialkoxybenzene derivatives by electrolysis, by electro-generated base (EG-base)-promoted Michael addition with CH2E2 (E = CO2R, COMe) in moderate to almost quantitative yield. The cyclohexenone derivatives were found to be a good precursor of benzofuranone derivatives through acid-promoted intramolecular lactonization.

Original languageEnglish
Pages (from-to)599-600
Number of pages2
JournalSynlett
Issue number6
Publication statusPublished - Jun 1998

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Derivatives
Electrolysis
Acids
2-cyclohexen-1-one

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "5-Substituted 4,4-dialkoxy-2-cyclohexen-1-ones were electro-synthesized from 4,4-disubstituted 2,5-cyclohexadien-1-ones, which were obtained from 1,4-dialkoxybenzene derivatives by electrolysis, by electro-generated base (EG-base)-promoted Michael addition with CH2E2 (E = CO2R, COMe) in moderate to almost quantitative yield. The cyclohexenone derivatives were found to be a good precursor of benzofuranone derivatives through acid-promoted intramolecular lactonization.",
author = "Sigeru Torii and Naoya Hayashi and Manabu Kuroboshi",
year = "1998",
month = "6",
language = "English",
pages = "599--600",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "6",

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T1 - Synthesis of 5-substituted 4,4-disubstituted 2-cyclohexen-1-ones by electro-generated base promoted Michael addition of 4,4-disubstituted 2,5-cyclohexadien-1-ones

AU - Torii, Sigeru

AU - Hayashi, Naoya

AU - Kuroboshi, Manabu

PY - 1998/6

Y1 - 1998/6

N2 - 5-Substituted 4,4-dialkoxy-2-cyclohexen-1-ones were electro-synthesized from 4,4-disubstituted 2,5-cyclohexadien-1-ones, which were obtained from 1,4-dialkoxybenzene derivatives by electrolysis, by electro-generated base (EG-base)-promoted Michael addition with CH2E2 (E = CO2R, COMe) in moderate to almost quantitative yield. The cyclohexenone derivatives were found to be a good precursor of benzofuranone derivatives through acid-promoted intramolecular lactonization.

AB - 5-Substituted 4,4-dialkoxy-2-cyclohexen-1-ones were electro-synthesized from 4,4-disubstituted 2,5-cyclohexadien-1-ones, which were obtained from 1,4-dialkoxybenzene derivatives by electrolysis, by electro-generated base (EG-base)-promoted Michael addition with CH2E2 (E = CO2R, COMe) in moderate to almost quantitative yield. The cyclohexenone derivatives were found to be a good precursor of benzofuranone derivatives through acid-promoted intramolecular lactonization.

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