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

Bradley O Ashburn; Rich G Carter

doi:10.1039/b714893c

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

Org Biomol Chem. 2008 Jan 21;6(2):255-7. doi: 10.1039/b714893c. Epub 2007 Nov 27.

Authors

Bradley O Ashburn¹, Rich G Carter

Affiliation

¹ Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, OR, USA.

PMID: 18174991
DOI: 10.1039/b714893c

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkynes / chemistry*
Biphenyl Compounds / chemical synthesis*
Biphenyl Compounds / chemistry
Cyclization
Molecular Structure
Nitro Compounds / chemistry*
Stereoisomerism

Substances

Alkynes
Biphenyl Compounds
Nitro Compounds
ortho-nitrophenylacetylene