A novel method for the synthesis of specifically substituted cycloheptatrienes

Abstract

Abstract A novel method has been developed for the synthesis of substituted cycloheptatrienes, involving the cycloaddition of substituted cyclopropenes to substituted thiophene 1,1‐dioxides followed by expulsion of sulfur dioxide from the cycloadduct. The scope and limitations of the reaction have been investigated and its mechanism is discussed. Attempts to extend this reaction principle to the synthesis of 1‐heterocycloheptatrienes were unsuccessful.

References

Page 1

	Year	Citations
The norcaradiene - cycloheptatriene equilibrium Roald Hoffmann Tetrahedron Letters Cycloheptatriene EquilibriumEngineeringHeterocyclicOrganic ChemistryChemistry	1970	253
Tropolone W. von E. Doering, Lawrence H. Knox Journal of the American Chemical Society AltmetricsSocial MediaOnline ReviewsInformationDatabases	1951	114
Transmission of substituent effects in anthracene. Acid dissociation constants of 10-substituted-9-anthroic acids and substituent chemical shifts of 10-substituted-9-fluoroanthracenes. Evidence for the .pi. inductive effect Gloria L. Anderson, Roger C. Parish, Leon M. Stock Journal of the American Chemical Society Derivative (Chemistry)Chemical MeasurementEngineeringChemical AnalysisBiochemistry	1971	88
SYNTHESIS OF TROPOLONE W. von E. Doering, Lawrence H. Knox Journal of the American Chemical Society Quantitative MethodsEngineeringMedia StandardsAltmetric Attention ScoreBibliometrics	1950	74
Synthesis of Substituted Tropolones W. von E. Doering, Lawrence H. Knox Journal of the American Chemical Society AltmetricsMedicineMass SpectrometryAltmetric Attention ScoreBibliometrics	1953	72
Dienes from 3-Pyrrolines. A Stereospecific Deamination David M. Lemal, Stanley D. McGregor Journal of the American Chemical Society Stereospecific DeaminationAltmetricsDonut IconMedicineAltmetric Attention Score	1966	65
Cyclopropenes as Reagents for Synthesis. Cycloaddition Reactions with Cyclopropenes M. L. Deem Synthesis DerivativesEngineeringHeterocyclicNatural SciencesDiversity-oriented Synthesis	1972	58
The first synthesis of monocyclic thiepins David N. Reinhoudt, C. G. KOUWENHOVEN Tetrahedron HeterocyclicEngineeringOrganic ChemistryNatural Product SynthesisBiomolecular Engineering	1974	54
Pyrolysis of 7,7-dibromobicyclo [4.1.0] heptane and derivatives D.G. Lindsay, Colin B. Reese Tetrahedron HeterocyclicDerivativesOrganic ChemistryChemistrySynthetic Chemistry	1965	50
Influence of Lewis acids on the Diels–Alder reaction. Part I. An improved synthesis of 7-azanorbornadiene, 3-azaquadricyclane, and azepine derivatives R. C. Bansal, A. W. McCulloch, A. G. McInnes Canadian Journal of Chemistry Dimethyl Acetylenedicarboxylate YieldsHeterocyclicLewis AcidsLaocoon Ii ProgramAlcl 3	1969	45

Page 1