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Spiropentadiene

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. :[[File:Spiropentadiene synthesis.svg|645px|Spiropentadiene synthesis]]

Derivatives

The derivative dichlorospiropentadiene has been reported. An all-silicon derivative (Si5 frame, (tBuMe2Si)3Si side groups) is also known. In contrast to the carbon parent this compound is stable with a melting point of 216 to 218 °C. The angle between the two rings as measured by X-ray single-crystal analysis is 78°.

References

References

  1. (1991). "Spiropentadiene". Journal of the American Chemical Society.
  2. (July 13, 1991). "Elusive bowtie pinned down - synthesis of spiropentadiene, a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie". Science News.
  3. (1999). "Synthesis and characterization of 1,4-dichlorospiropentadiene". Tetrahedron Letters.
  4. (2000). "A Stable Bicyclic Compound with Two Si=Si Double Bonds". Science.
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cyclopropenes spiro-compounds dienes polycyclic-nonaromatic-hydrocarbons substances-discovered-in-the-1990s
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