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 hydr...

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Bibliographic Details
Main Authors: Bradford, T., Payne, Alan, Willis, A., Paddon-Row, M., Sherburn, M.
Format: Journal Article
Published: American Chemical Society 2010
Subjects:
Online Access:http://hdl.handle.net/20.500.11937/6896
Description
Summary: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 Diets-Alder reactivity of [3]dendralene-including double cycloaddition sequences and catalytic enantio selective variant-are reported.