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.
|Number of pages||3|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 2004 May 28|
ASJC Scopus subject areas
- Organic Chemistry