Generation and Reactions of 5,6-Dimethylene-2-cyclohexene-1,4-diones. A New Synthesis of Polycyclic 1,4-Benzoquinones

doi:10.1246/BCSJ.57.615

Paper

Generation and Reactions of 5,6-Dimethylene-2-cyclohexene-1,4-diones. A New Synthesis of Polycyclic 1,4-Benzoquinones

Published 1984 · Yoshinori Kanao, Masaji Oda

Bulletin of the Chemical Society of Japan

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6

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0

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Abstract

1,2,3,6-Tetrahydrobenzocyclobutene-3,6-dione underwent thermal ring opening of the four-membered ring at 140°C to generate 5,6-dimethylene-2-cyclohexene-1,4-dione. This is a highly reactive substance and was trapped as dimers or Diels-Alder adducts giving polycyclic 1,4-benzoquinones. Intramolecular rearrangements preferably took place in some derivatves.

Study Snapshot

This study presents a new method for synthesis of polycyclic 1,4-benzoquinones using 5,6-dimethylene-2-cyclohexene-1,4-dione, a highly reactive substance with potential applications in various fields.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Generation and Reactions of 5,6-Dimethylene-2-cyclohexene-1,4-diones. A New Synthesis of Polycyclic 1,4-Benzoquinones

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References

Citations

On the tendency of 1,2,3,6-tetrahydrobenzocyclobutene-3,6-diones for undergoing site-selective Diels-Alder reactions at the internal double bond

Cyclobutene-3,6-diones exhibit site-selective Diels-Alder reactions at the internal double bond due to strain effects rather than frontier orbital effects.

1-Substituted 3,6-Dihydroxybenzocyclobutene. A Versatile Precursor of Naturally Occurring Quinones

1-Substituted 3,6-Dihydroxybenzocyclobutene is a versatile precursor for naturally occurring quiones, offering efficient routes to various compounds using photoaddition, reduction, and dehydrochlorination.

SYNTHESIS AND SOME PROPERTIES OF 1,2-DIHYDRO-4,7-DIHYDROXYCYCLOBUTA[b]NAPHTHALENE-3,8-DIONE AND 1,2,5,6-TETRAHYDRO-4,7-DIHYDROXYDICYCLOBUTA[b,g]NAPHTHALENE-3,8-DIONE

The synthesized compounds show strain effects on 13C NMR chemical shifts, tautomeric equilibrium, reduction potentials, and Diels-Alder reactions, leading to novel polycyclic hydroxyquinones.