Microwave-assisted intramolecular [2 + 2] Allenic cycloaddition reaction for the rapid assembly of bicyclo[4.2.0]octa-1,6-dienes and bicyclo[5.2.0]nona-1,7-dienes.
Microwave irradiation of alkynyl allenes affords an intramolecular [2 + 2] cycloaddition reaction. This cycloaddition provides an efficient route to bicyclomethylenecyclobutenes. The reaction occurs with complete regioselectivity for the distal double bond of the allene for the selective formation of a variety of hetero- and carbocyclic substrates. Bicyclo[4.2.0]octadienes and bicyclo[5.2.0]nonadienes have been prepared in high yield. [reaction: see text]
Brummond
Kay M
KM
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. kbrummon@pitt.edu
Chen
Daitao
D
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008872:Microwaves; D015394:Molecular Structure
D000475:Alkenes; D001643:Bridged Bicyclo Compounds