Spiropentadiene, or bowtiediene, is a hydrocarbon with formula C 5H 4. 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.[1][2]
The derivative dichlorospiropentadiene has been reported.[3] An all-silicon derivative (Si5 frame, (tBuMe2Si)3Si side groups) is also known.[4] 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°.
Referencesedit
^Billups, W. E.; Haley, M. M. (1991). "Spiropentadiene". Journal of the American Chemical Society. 113 (13): 5084. doi:10.1021/ja00013a067.
^. Science News. July 13, 1991. Archived from the original on 2022-02-16.
^Saini, R.; Litosh, V.; Daniels, A.; Billups, W. (1999). "Synthesis and characterization of 1,4-dichlorospiropentadiene". Tetrahedron Letters. 40 (34): 6157. doi:10.1016/S0040-4039(99)01293-9.
^Iwamoto, T.; Tamura, M.; Kabuto, C.; Kira, M. (2000). "A Stable Bicyclic Compound with Two Si=Si Double Bonds". Science. 290 (5491): 504–506. Bibcode:2000Sci...290..504I. doi:10.1126/science.290.5491.504. PMID 11039928.
March 14, 2024
spiropentadiene, bowtiediene, hydrocarbon, with, formula, simplest, spiro, connected, diene, very, unstable, decomposing, even, below, high, bond, strain, does, occur, nature, synthesis, reported, 1991, namespreferred, iupac, name, spiro, penta, dieneother, na. Spiropentadiene or bowtiediene is a hydrocarbon with formula C5 H4 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 1 2 Spiropentadiene NamesPreferred IUPAC name Spiro 2 2 penta 1 4 dieneOther names Bowtiediene Spiropenta 1 4 dieneIdentifiersCAS Number 1727 65 7 Y3D model JSmol Interactive imageChemSpider 35807558PubChem CID 14901520CompTox Dashboard EPA DTXSID80565167InChI InChI 1S C5H4 c1 2 5 1 3 4 5 h1 4HKey JXGJFWLYGSVFBS UHFFFAOYSA NSMILES C1 CC21C C2PropertiesChemical formula C 5H 4Molar mass 64 087 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSynthesis editSpiropentadiene 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 nbsp Derivatives editThe derivative dichlorospiropentadiene has been reported 3 An all silicon derivative Si5 frame tBuMe2Si 3Si side groups is also known 4 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 edit Billups W E Haley M M 1991 Spiropentadiene Journal of the American Chemical Society 113 13 5084 doi 10 1021 ja00013a067 Elusive bowtie pinned down synthesis of spiropentadiene a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie Science News July 13 1991 Archived from the original on 2022 02 16 Saini R Litosh V Daniels A Billups W 1999 Synthesis and characterization of 1 4 dichlorospiropentadiene Tetrahedron Letters 40 34 6157 doi 10 1016 S0040 4039 99 01293 9 Iwamoto T Tamura M Kabuto C Kira M 2000 A Stable Bicyclic Compound with Two Si Si Double Bonds Science 290 5491 504 506 Bibcode 2000Sci 290 504I doi 10 1126 science 290 5491 504 PMID 11039928 Retrieved from https en wikipedia org w index php title Spiropentadiene amp oldid 1189902158, wikipedia, wiki, book, books, library,
