53011-95-3

Basic information

• Product Name: 2,3-dimethylidene-7-oxabicyclo[2.2.1]heptane
• Synonyms: 2,3-Bis(methylene)-7-oxabicyclo[2.2.1]heptane; 7-Oxabicyclo(2.2.1)heptane, 2,3-bis(methylene)-; 7-oxabicyclo[2.2.1]heptane, 2,3-bis(methylene)-
• CAS NO: 53011-95-3
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.1644
• Mol File: 53011-95-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 170.3°C at 760 mmHg
• Flash Point: 49°C
• Density: 1g/cm³
• Vapor Pressure: 1.97mmHg at 25°C
• Refractive Index: 1.502
• CAS DataBase Reference: 2,3-dimethylidene-7-oxabicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethylidene-7-oxabicyclo[2.2.1]heptane(53011-95-3)
• EPA Substance Registry System: 2,3-dimethylidene-7-oxabicyclo[2.2.1]heptane(53011-95-3)

Safety Data

• Hazardous Substances Data: 53011-95-3(Hazardous Substances Data)

Upstream product

• 81486-04-6 2-endo,3-exo-Bis(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-5-ene 
• 55423-53-5 (2-endo,3-exo)-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol 
• 81486-09-1 (2-endo,3-exo)-7-oxabicyclo<2.2.1>hept-5-ene-2,3-bis(carbonyl chloride) 
• 29745-04-8 norcantharidin 
• 55423-53-5 (exo,exo)-7-oxabicyclo[2.2.1]-heptane-2,3-dimethanol 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 97909-51-8 (2-endo,3-exo)-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol bis(4-methylbenzenesulfonate) 

Downstream Products

• 95-13-6 1-indene 
• 98652-59-6 (1S*,2S*,7R*,8R*,9R*)-2-methyl-8,9-bis(phenylsulfonyl)tricyclo<6.2.2.0^1.6>undeca-5,10-diene 
• 98652-59-6 (1S*,2S*,7R*,8S*,9S*)-2-methyl-8,9-bis(phenylsulfonyl)tricyclo<6.2.2.0^1.6>undeca-5,10-diene 
• 98652-56-3 4-phenyl-5,6-dihydro-4H-indene 
• 108635-92-3 1-ethynyl-2-pentylbenzene 
• 105243-79-6 2-methylidene-3-<(Z)-(2-nitrophenylsulfenyl)methylidene>-7-oxabicyclo<2.2.1>heptane 

Relevant articles and documents

THE 1,7-CYCLOHEXENONORBORNADIENE SYSTEM

2,3-Dimethylene-7-oxabicycloheptane, available by reduction and dehydration of the furan-fumaroyl chloride Diels-Alder adduct, undergoes ready dibromocyclopropanation at one of its exocyclic double bonds.The corresponding carbenoid, generated by reaction of the dibromide with 4 equiv of an organolithium reagent, undergoes the Skatteboel rearrangement to provide a fused cyclopentadiene ring which is immediately deprotonated.This anion fragments to a fulvene alkoxide to which the organolithium reagent subsequently adds.The resulting anion, namely 9, provides fulvenes of type 3 on workup.The use of 3 as a diene in Diels-Alder cycloadditions is demonstrated by the condensation of methyl derivative 3a with dimethyl acetylenedicarboxylate and (E)-1,2-bis(phenylsulfonyl)ethylene.The question of face selectivity is raised.For the bissulfone adducts 21 and 22, reductive desulfonylation with 1-2percent sodium amalgam delivers hydrocarbon 23, the first known member of the 1,7-cycloalkenonorbornadiene class of molecules. (13)C-NMR measurements show that 23 is as polarized as its simple non-annulated prototype and is unstrained.