Naphtho[1,2-c:5,6-c]difuran: a reactive linker and cyclophane precursor.
Naphtho[1,2-c:5,6-c]difuran has been isolated in a 9-step synthesis from 2,6-dimethylnaphthalene. It is a highly reactive diene similar in nature to the related isobenzofuran. In Diels-Alder reactions, its intermediate monoadducts are actually less reactive that the parent difuran making possible sequential Diels-Alder reactions with different dienophiles. Reaction with a tethered bis(dienophile) leads to the production of a naphthalenic cyclophane.
Thibault
Michelle E
ME
Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, Canada T1K 3M4.
Closson
Taunia L L
TL
Manning
Sidney C
SC
Dibble
Peter W
PW