Synthesis of 1,2-disubstituted naphthalenes and tetrahydronaphthalenes from dihydronaphthalenes obtained by conjugate addition of organolithium reagents to 2,6-bis(tert-butyl)-4-methoxyphenyl naphthalenecarboxylates

Mitsuru Shindo, Kenji Koga, Kiyoshi Tomioka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A method of the conversion of 2,6-bis(tert-butyl)-4-methoxyphenyl dihydronaphthalenecarboxylates into substituted naphthalenes and tetrahydronaphthalenes was developed. Aromatization of substituted dihydronaphthalenecarboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and subsequent treatment with ceric ammonium nitrate (CAN) gave the corresponding substituted naphthalenecarboxylic acids. Alternatively, hydrogenolysis and subsequent treatment with CAN provided a way to tetrahydronaphthalenemethanols in good yields.

Original languageEnglish
Pages (from-to)1318-1321
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number9
DOIs
Publication statusPublished - Jan 1 1999
Externally publishedYes

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Tetrahydronaphthalenes
Naphthalenes
Aromatization
Hydrogenolysis
Acids
ceric ammonium nitrate

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

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title = "Synthesis of 1,2-disubstituted naphthalenes and tetrahydronaphthalenes from dihydronaphthalenes obtained by conjugate addition of organolithium reagents to 2,6-bis(tert-butyl)-4-methoxyphenyl naphthalenecarboxylates",
abstract = "A method of the conversion of 2,6-bis(tert-butyl)-4-methoxyphenyl dihydronaphthalenecarboxylates into substituted naphthalenes and tetrahydronaphthalenes was developed. Aromatization of substituted dihydronaphthalenecarboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and subsequent treatment with ceric ammonium nitrate (CAN) gave the corresponding substituted naphthalenecarboxylic acids. Alternatively, hydrogenolysis and subsequent treatment with CAN provided a way to tetrahydronaphthalenemethanols in good yields.",
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T1 - Synthesis of 1,2-disubstituted naphthalenes and tetrahydronaphthalenes from dihydronaphthalenes obtained by conjugate addition of organolithium reagents to 2,6-bis(tert-butyl)-4-methoxyphenyl naphthalenecarboxylates

AU - Shindo, Mitsuru

AU - Koga, Kenji

AU - Tomioka, Kiyoshi

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AB - A method of the conversion of 2,6-bis(tert-butyl)-4-methoxyphenyl dihydronaphthalenecarboxylates into substituted naphthalenes and tetrahydronaphthalenes was developed. Aromatization of substituted dihydronaphthalenecarboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and subsequent treatment with ceric ammonium nitrate (CAN) gave the corresponding substituted naphthalenecarboxylic acids. Alternatively, hydrogenolysis and subsequent treatment with CAN provided a way to tetrahydronaphthalenemethanols in good yields.

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