1975
DOI: 10.1021/jo00905a006
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7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dione and its radical anion. Experimental and theoretical study

Abstract: The synthesis of 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dione (2a) and its 1-methyl derivative is described. Electrolytic reduction of 2a gives its radical anion which has a large bridgehead hydrogen coupling of 2.48 G. Using the INDO method with a MINDO/2' optimized geometry, spin densities for 2a•are calculated and partitioned into their spin polarization and spin delocalization components. Mechanisms for the interaction of the vinyl and bridgehead hydrogens in 2a•-with the unpaired electron are discussed based o… Show more

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Cited by 9 publications
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“…One promising class of monomers for the facile generation of conjugated polymers via ROMP are norbornenes 1 and 2 (Chart ). These monomers can be readily prepared via Diels−Alder reaction of cyclopentadiene or furan with dichlorovinylene carbonate.…”
Section: Introductionmentioning
confidence: 99%
“…One promising class of monomers for the facile generation of conjugated polymers via ROMP are norbornenes 1 and 2 (Chart ). These monomers can be readily prepared via Diels−Alder reaction of cyclopentadiene or furan with dichlorovinylene carbonate.…”
Section: Introductionmentioning
confidence: 99%