17684-75-2

Basic information

• Product Name: Bicyclo[3.2.2]nona-3,6,8-trien-2-one
• CAS NO: 17684-75-2
• Molecular Formula: C9H8O
• Molecular Weight: 132.162
• Mol File: 17684-75-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Bicyclo[3.2.2]nona-3,6,8-trien-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.2.2]nona-3,6,8-trien-2-one(17684-75-2)
• EPA Substance Registry System: Bicyclo[3.2.2]nona-3,6,8-trien-2-one(17684-75-2)

Safety Data

• Hazardous Substances Data: 17684-75-2(Hazardous Substances Data)

Upstream product

• 38276-33-4 C₁₇H₁₆O₆ 
• 539-80-0 Tropone 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 15598-76-2 cycloheptatrienylacetyl chloride 

Downstream Products

• 81044-32-8 C₁₆H₁₅N₂O₂S^(1-)*Li⁽¹⁺⁾ 
• 81044-34-0 tricyclo<6.1.0.0^4,9>nona-2,6-dien-5-one tosylhydrazone 
• 75085-64-2 (2R,5R,9S)-3-Phenyl-tricyclo[3.3.1.0^2,8]nona-3,6-diene-9-carbonitrile 
• 75085-65-3 (2R,5S,9R)-4-Phenyl-tricyclo[3.3.1.0^2,8]nona-3,6-diene-9-carbonitrile 
• 345228-28-6 bicyclo<3.2.2>nona-3,6,9-trien-2-one tosylhydrazone 
• 75073-69-7 2-phenyl-bicyclo<3.2.2>nona-3,6,8-triene-2-ol 
• 38898-62-3 tricyclo<6.1.0.0^4,9>nona-2,6-dien-5-one 
• 83-33-0 inden-1-one 

Relevant articles and documents

Structural Fluxionality in the Tricyclo2,8>nona-3,6-dienyl and Bicyclonona-2,6,8-trienyl Radicals

E.s.r observation of radicals derived from 9-bromtricyclo2,8>nona-3,6-diene, and related compounds, showed that they rearrange by β-scission to bicyclonona-2,6,8-trienyl radicals extremly rapidly; the latter radicals have hyperfine splittings similar to those of allyl radicals. 9-Deuterio- and 2-deuterio-9-bromotricyclo2,8>nona-3,6-diene were reduced with tributyltin hydride.The pattern of deuterium scrambling in the bicyclonona-2,6,8-triene and tricyclo2,8>nona-3,6-diene products showed that the intermediate radicals take part in a degenerate rearrangement sequence which makes them fully fluxional in three dimensions.The two radicals are in equilibrium at ca. 375 K, but the bicyclotrienyl species is more important by a factor of ca. 102.Neither the experimental results nor MNDO semiempirical calculations provided any evidence of additional thermodynamic stabilisation in the radical pair beyond that expected for allyl delocalisation.

Novel Two-Step Synthesis of Homobarrelenones, Bicyclonona-3,6,8-trien-2-ones, from Tropones and 2,3-Bis(methoxycarbonyl)-7-oxabicyclohepta-diene by High-Pressure Cycloaddition-Thermal Cyclorevision Procedure

The Diels-Alder adduct of tropone with 2,3-bis(methoxycarbonyl)-7-oxabicyclohepta-2,5-diene formed homobarrelenone by heating at ca. 130 deg C.Similarly prepared were 1-hydroxy-, 3-methoxy-, 1-chloro-, and 3-chlorohomobarrelenones.High-pressure cycloaddition improved the yields of the Diels-Alder adducts.