Diels-Alder approach to biaryls (DAB): importance of the ortho-nitro moiety in the [4 + 2] cycloaddition.
A series of nitrophenyl acetylenes were evaluated for their utility in a cycloaddition-cycloreversion approach to polysubstituted biaryls. ortho-Nitrophenyl acetylene consistently provided the target biaryls in superior yields as compared to the meta and para nitro substituted variants.
Ashburn
Bradley O
BO
Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, OR, USA.
Carter
Rich G
RG
D000480:Alkynes / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001713:Biphenyl Compounds; D009574:Nitro Compounds; C527559:ortho-nitrophenylacetylene