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Tetravinylallene is an acyclic hydrocarbon with 11 carbon atoms and six double bonds. In 2019, chemists reported synthesizing it in six steps. The molecule is notable not just for its unusually high number of double bonds, but for how it can be used in successive reactions to build complex, multi-ring structures. The report cautioned that it might be the most double-bond-rich acyclic hydrocarbon synthesized to date.
What is tetravinylallene?
Tetravinylallene is a hydrocarbon: a molecule made only of carbon and hydrogen. Its 11 carbon atoms form an acyclic structure, meaning the molecule itself does not contain a carbon ring, and it has six carbon–carbon double bonds. The name reflects its relationship to allene chemistry. An allene contains two adjacent double bonds that share a central carbon; tetravinylallene combines that motif with four vinyl groups.
Chemistry World reported the compound and its synthesis in 2019, describing it cautiously as a possible record-holder rather than establishing an unqualified record. Chemistry World’s report attributes the work to C. Elgindy, J. S. Ward, and M. S. Sherburn.
How was it synthesized?
The reported synthesis took six steps. The Chemistry World account says the researchers needed extensive experimentation to establish workable conditions, but it does not give the reaction conditions or yields. The available report therefore supports the step count and the difficulty of developing the route, not a detailed reconstruction of the laboratory procedure.
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Why does the molecule matter?
Its six double bonds offer multiple opportunities for pericyclic reactions, a class of reactions in which bonds reorganize through a cyclic arrangement of atoms. In particular, successive Diels–Alder reactions can turn an open-chain starting material into a more elaborate ring system.
A two-step route to a complex structure
In a reported sequence, four pericyclic reactions took place over two steps, forming four rings, seven carbon–carbon bonds, and nine stereocentres. Stereocentres are atoms at which different three-dimensional arrangements are possible. Building several rings and stereocentres in a short sequence illustrates why chemists were interested in tetravinylallene as a platform for molecular construction.
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Earlier allene chemistry provides context
The report also describes a prior synthesis of the marine natural product pseudopterosin using 1,1-divinylallene. That route reduced the reported synthesis from 20 steps to 11. This is background on the broader strategy of using polyunsaturated building blocks to assemble rings; it is not the step count for making tetravinylallene.
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Is tetravinylallene stable?
No. The 2019 report says tetravinylallene was unstable in air and when stored as a neat liquid—that is, in its undiluted form. It should not be portrayed as a stable, readily handled substance. The account does not specify storage conditions or provide a practical handling protocol.
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What the 2019 report establishes—and what it does not
The report establishes the headline features: an 11-carbon acyclic hydrocarbon with six double bonds, a six-step synthesis, instability in air or as a neat liquid, and a demonstrated sequence that built four rings and nine stereocentres. It does not provide the experimental details needed to reproduce the synthesis, including reaction conditions and yields. The underlying paper is attributed to C. Elgindy, J. S. Ward, and M. S. Sherburn in Angewandte Chemie International Edition (2019), DOI 10.1002/anie.201908496.
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