Diels-Alder approach to biaryls (DAB): importance of the ortho-nitro moiety in the [4 + 2] cycloaddition

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.

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Veröffentlicht in:Organic & biomolecular chemistry 2008-01, Vol.6 (2), p.255-257
Hauptverfasser: Ashburn, Bradley O, Carter, Rich G
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Biphenyl Compounds - chemical synthesis
Biphenyl Compounds - chemistry
Cyclization
Molecular Structure
Nitro Compounds - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b714893c