Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Hisato Shimizu, Akira Yoshimura, Keiichi Noguchi, Victor N. Nemykin, Viktor V. Zhdankin, Akio Saito

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

Original languageEnglish
Pages (from-to)531-536
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - 28 Feb 2018

Fingerprint

Benzoquinones
Hydroxamic Acids
Guaiacol
Cycloaddition
Benzene
Iodine
(bis(trifluoroacetoxy)iodo)benzene

Keywords

  • Acylnitroso
  • Benzoquinone
  • Cycloaddition
  • Dearomatization
  • Iodine(III)

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents. / Shimizu, Hisato; Yoshimura, Akira; Noguchi, Keiichi; Nemykin, Victor N.; Zhdankin, Viktor V.; Saito, Akio.

In: Beilstein Journal of Organic Chemistry, Vol. 14, 28.02.2018, p. 531-536.

Research output: Contribution to journalArticle

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