A simple radical addition - Elimination route to geometrically pure (E)-alkene and chromanone derivatives via β-nitrostyrene

Yeong Jiunn Jang, Ming Chung Yan, Yung Feng Lin, Ching-Fa Yao

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Various geometrically pure (E)-β-alkyl-styrenes have been synthesized by the radical NO 2 substitution of alkyl moieties generated via hydrogen abstraction followed by decarbonylation from aliphatic aldehydes. These reactions, which involve a high chemical selectivity and regioselectivity constitute a new route to (E)-β-alkylstyrenes. Both aliphatic and aromatic aldehydes can be used in this novel reaction. When 2-allyloxybenzaldehyde was used, the benzoyl radical added directly to the double bond without decarbonylation to give the 3-cinnamylchroman-4-one. This unique difference between aliphatic and aromatic aldehydes represents a simple route for the synthesis of biologically important chromanones.

Original languageEnglish
Pages (from-to)3961-3963
Number of pages3
JournalJournal of Organic Chemistry
Issue number11
Publication statusPublished - 2004 May 28


ASJC Scopus subject areas

  • Organic Chemistry

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