Practical synthesis and reactivity of [3]dendralene.
A convenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diels-Alder reactivity of [3]dendralene--including double cycloaddition sequences and catalytic enantioselective variant--are reported.
Bradford
Tanya A
TA
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
Payne
Alan D
AD
Willis
Anthony C
AC
Paddon-Row
Michael N
MN
Sherburn
Michael S
MS