7092-05-9

Basic information

• Product Name: tricyclo[3.2.2.0~2,4~]nona-6,8-diene
• CAS NO: 7092-05-9
• Molecular Formula: C₉H₁₀
• Molecular Weight: 118.1757
• Mol File: 7092-05-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 166.2°C at 760 mmHg
• Flash Point: 32°C
• Density: 1.091g/cm³
• Vapor Pressure: 2.38mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: tricyclo[3.2.2.0~2,4~]nona-6,8-diene(CAS DataBase Reference)
• NIST Chemistry Reference: tricyclo[3.2.2.0~2,4~]nona-6,8-diene(7092-05-9)
• EPA Substance Registry System: tricyclo[3.2.2.0~2,4~]nona-6,8-diene(7092-05-9)

Safety Data

• Hazardous Substances Data: 7092-05-9(Hazardous Substances Data)

Upstream product

• 944-41-2 (3aα,4β,4aα,5aα,6β,6aα)-4,4a,5,5a,6,6a-hexahydro-4,6-etheno-1H-cycloprop[f]isobenzofuran-1,3(3aH)-dione 
• 83818-44-4 anti-6,7-bis(phenylsulfonyl)tricyclo<3.2.2.0^2,4>non-8-ene 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 108-31-6 maleic anhydride 

Downstream Products

• 27367-72-2 exo,exo-bishomobarrelene 
• 27335-51-9 endo,exo-bishomobarrelene 

Relevant articles and documents

Metallated Bicyclonona-2,6,8-trienes, Their Rearrangement to Barbaralanes, and a Short Synthesis of the Bicyclonona-2,6,8-trien-4-yl Anion

Five different anions are formed when bicyclonona-2,6,8-triene (1a) is deprotonated: the 6- and 7-yl anions when using tBuLi/TMEDA, the 4,6- and 4,7-diyl dianions when using nBuLi/tBuOK, and the 4-yl anion (1-) after quenching the dianions with THF.Reaction of the anions with Me3SnCl gives the 6-, 7-, and 4-monostannylated bicyclonona-2,6,8-trienes 1b, 1c, and 1d as well as the exo-4,7-, endo-4,6-, and endo-4,7-distannylated bicyclonona-2,6,8-trienes 1e, 1f, and 1g, respectively.Reaction of 1- with Me3SiCl and Me3PbCl leads to the corresponding 4-silyl derivative 1h and its plumbyl analogue 1i.Inversely, cleavage of 1d with MeLi allows to generate 1- under particularly mild conditions.The metallation of tricyclo2,4>nona-6,8-diene (3a), which was tested for an alternative route to 1-, gives two stannyl derivatives 3b and 3c which are substituted in the vinylic positions. - On heating 1d and 1i rearrange to yield 9-trimethylstannylbarbaralane (2d) and its plumbyl analogue 2i quantitatively.The reactivity decreases on passing from 1i to 1d whereas 1h does not react.Mercury and zinc derivatives of 1- are so labile that only dibarbaralylmercury (2j) and -zinc (2k) are observed by NMR spectroscopy.The title rearrangement proceeds by a 1,5-homodienyl metallatropic shift which involves an endo-type transition structure. - The new compounds 1b - i, 2d, 2i, 3b and 3c are characterized with emphasis on the NMR data including 1H, 13C, 119Sn, 207Pb signal shifts and various heteronuclear couplings.Key Words: Deprotonation / 1,5-Homodienyl shift / Bicyclonona-2,6,8-trienes / Tricyclo2,4>nona-6,8-dienes / Barbaralanes

cis-1,2-Bis(phenylsulfonyl)ethylene: a Novel, Convenient Acetylene Synthon in Diels-Alder Reactions

cis-1,2-Bis(phenylsulfonyl)ethylene (5) is found to be a reactive acetylene synthon in Diels-Alder reactions since, after cycloaddition to cyclopentadiene, cyclohexadiene, and cycloheptatriene, and reduction with sodium amalgam, the corresponding bicyclodienes (6)-(8) are obtained in good yields.