Practical Synthesis of the Dendralene Family Reveals Alternation in Behavior

2009/05/19 by Alan D. Payne, Gomotsang Bojase, Michael N. Paddon‐Row +1 · 7 citations
Chemistry · #Synthetic Organic Chemistry Methods #Synthesis and Properties of Aromatic Compounds #Organometallic Complex Synthesis and Catalysis

paper · doi:10.1002/anie.200901733

openalex publication_date 2009/05/19 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02

Abstract

Back from obscurity: The practical synthesis of the first six members of the fundamental class of acyclic branched oligoalkenes has been achieved. The syntheses allow access to the target compounds on multigram scales in good yields. Members of the family with even numbers of double bonds are significantly more stable than those with odd numbers (see picture), and exhibit different chemical reactivities in Diels-Alder reactions.

Citations

• Molecular Structure of 3,4-Dimethylenehexa-1,5-diene ([4]Dendralene), C8H10, in the Gas Phase As Determined by Electron Diffraction and ab Initio Calculations

Cited by

• Preparation and Synthetic Value of π-Bond-Rich Branched Hydrocarbons
• Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes
• Practical Synthesis and Reactivity of [3]Dendralene
• Synthesis and Diels–Alder Reactivity of Substituted [4]Dendralenes
• Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions
• Unexpected Formation of a [4]Radialene and Dendralenes by Addition of Tetracyanoethylene to a Tetraaryl[5]cumulene
• Dendralene [wikipedia]

Related

• Preparation and Synthetic Value of π-Bond-Rich Branched Hydrocarbons
• Practical Synthesis and Reactivity of [3]Dendralene
• Synthesis and Diels–Alder Reactivity of Substituted [4]Dendralenes
• Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes
• Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions