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spiropentadiene
Sign in to saveAlso known as spiro[2.2]penta-1,4-diene
Spiropentadiene, or bowtiediene, is a hydrocarbon with formula . The simplest spiro-connected diene, it is very unstable—decomposing even below −100 °C—due to its high bond strain and does not occur in nature. Its synthesis was reported in 1991.
Chemical data
- Formula
- C5H4
- Molecular weight
- 64.08 g/mol
- IUPAC name
- spiro[2.2]penta-1,4-diene
- SMILES
- C1=CC12C=C2
- InChIKey
- JXGJFWLYGSVFBS-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- spiro compound
- Mass
- 64.0313
Show 3 more facts
- chemical formula
- C₅H₄
- canonical SMILES
- C1=CC12C=C2
- Commons category
- Spiropentadiene
Sources (2)
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Encyclopedic overview
3 sectionsContents
- Synthesis
- Derivatives
- References
Spiropentadiene, or bowtiediene, is a hydrocarbon with formula . The simplest spiro-connected diene, it is very unstable—decomposing even below −100 °C—due to its high bond strain and does not occur in nature. Its synthesis was reported in 1991.
==Synthesis== Spiropentadiene was synthesised from bistrimethylsilylpropynone 1 by reaction with p-toluenesulfonylhydrazide to tosylhydrazone 2 followed by treatment with sodium cyanoborohydride to allene 3 and followed by two successive reactions with chlorocarbene generated from methyllithium and dichloromethane to spiro compound 5. Spiropentadiene was trapped in a liquid nitrogen trap after reaction with TBAF in a double elimination reaction. 645px|Spiropentadiene synthesis
Excerpted from Wikipedia’s “spiropentadiene” article, available under the CC BY-SA 4.0 licence.
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