Improved one-pot synthesis of styryl tetrahydrofurans and cyclohexanes by radical addition to β-nitrostyrenes in the presence of benzoyl peroxide

Yeong Jiunn Jang, Yuh Kuo Shih, Jing Yuan Liu, Wen Yu Kuo, Ching-Fa Yao

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Stereoselective styryl derivatives have been prepared based on radical substitution (addition-elimination) of heterocycles or cyclohydrocarbons units to (E)-β-nitrostyrenes 1 using a common radical initiator benzoyl peroxide. High reactivity and selectivity with wide substrate scope were attained by using this easy methodology. The reactions using easily obtained and one-pot potential starting materials gave excellent trans-selectivity with medium to high yields in all cases. Synthetic utility of this approach has been demonstrated by the preparation of various trans-styryl derivatives.

Original languageEnglish
Pages (from-to)2123-2128
Number of pages6
JournalChemistry - A European Journal
Volume9
Issue number9
DOIs
Publication statusPublished - 2003 May 9

Fingerprint

Cyclohexanes
Benzoyl Peroxide
Furans
Derivatives
Substitution reactions
Substrates

Keywords

  • Alkenes
  • Heterocycles
  • Peroxides
  • Radical reactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Improved one-pot synthesis of styryl tetrahydrofurans and cyclohexanes by radical addition to β-nitrostyrenes in the presence of benzoyl peroxide. / Jang, Yeong Jiunn; Shih, Yuh Kuo; Liu, Jing Yuan; Kuo, Wen Yu; Yao, Ching-Fa.

In: Chemistry - A European Journal, Vol. 9, No. 9, 09.05.2003, p. 2123-2128.

Research output: Contribution to journalArticle

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AU - Yao, Ching-Fa

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