Novel reactivity of SeO2 with 1,3-dienes: selenophene formation.
A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Truc M
TM
Nguyen
Ilia A
IA
Guzei
Daesung
D
Lee
D000475:Alkenes / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D018036:Selenium Compounds / Q000737:chemistry*; D064588:Selenium Oxides
D000475:Alkenes; D016566:Organoselenium Compounds; D018036:Selenium Compounds; D064588:Selenium Oxides