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Volumn 35, Issue 4, 1970, Pages 1155-1165

Photochemical and Thermal 1,2- and 1,4-Cycloaddition Reactions of Azodicarbonyl Compounds with Monoolefins

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EID: 0009486259     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00829a065     Document Type: Article
Times cited : (100)

References (87)
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    • references therein
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    • Detailed discussions with Professor Fahr prior to publication are gratefully appreciated
    • Detailed discussions with Professor Fahr prior to publication are gratefully appreciated. J. Markert and E. Fahr, Tetrahedron Lett.y 769 (1970).
    • (1970) Tetrahedron Lett.y , pp. 769
    • Markert, J.1    Fahr, E.2
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    • Anderson kindly provided us with a copy of his manuscript prior to publication
    • J. E. Anderson and J. M. Lehn, Tetrahedron, 24, 123 (1968); 24, 137 (1968). Dr, J. E. Anderson kindly provided us with a copy of his manuscript prior to publication.
    • (1968) Tetrahedron , vol.24 , pp. 123
    • Anderson, J.E.1    Lehn, J.M.2
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    • We are grateful to Professor Sauer for detailed information about his procedure prior to publication, and for a generous sample of PTD
    • We are grateful to Professor Sauer for detailed information about his procedure prior to publication, and for a generous sample of PTD. R. C. Cookson, S. S. H. Gilani, and I. D. R. Stevens, J. Chem. Soc., C 1905 (1967).
    • (1967) J. Chem. Soc., C , pp. 1905
    • Cookson, R.C.1    Gilani, S.S.H.2    Stevens, I.D.R.3
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    • 4 reduction to 28, and have proven cis configuration for 28 by chemical means. Correspondence with Dr. Huebner, who kindly postponed the publication of his paper to allow the simultaneous appearance of our work is gratefully appreciated
    • 4 reduction to 28, and have proven cis configuration for 28 by chemical means. Correspondence with Dr. Huebner, who kindly postponed the publication of his paper to allow the simultaneous appearance of our work is gratefully appreciated.
    • (1970) J. Org. Chem. , vol.35 , pp. 1149
    • Huebner, C.F.1    Donoghue, E.M.2    Novak, C.J.3    Dorfman, L.4    Wenkert, E.5
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    • valuable discussions with Professor Gompper, who kindly provided a manuscript prior to publication, are gratefully appreciated
    • Angew. Chem. Int. Ed. Engl., 8, 312 (1969); valuable discussions with Professor Gompper, who kindly provided a manuscript prior to publication, are gratefully appreciated.
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    • E. Fahr, and J. Flemming, as well as C. F. Huebner and his collaborators, have obtained 20 from indene and PTD in acetone according to private communications, but were unable to isolate 21. We are grateful to Professor Fahr for a copy of the thesis of J. Flemming, Würzburg University, 1967. Note Added in Proof.-Compound 21 was obtained also by Würzburg University
    • E. Fahr, and J. Flemming, as well as C. F. Huebner and his collaborators, have obtained 20 from indene and PTD in acetone according to private communications, but were unable to isolate 21. We are grateful to Professor Fahr for a copy of the thesis of J. Flemming, Würzburg University, 1967. Note Added in Proof.-Compound 21 was obtained also by H. Helfert, Thesis, Würzburg University, 1969.
    • (1969) Thesis
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    • Difference between the experimentally determined molecular refraction and the calculated molecular refraction (using atomic refraction constants but omitting the C=C increment). For a detailed discussion of this experimental measure of the C=C bond polarizability see Cornell University Press, Ithaca, N. Y.
    • Difference between the experimentally determined molecular refraction and the calculated molecular refraction (using atomic refraction constants but omitting the C=C increment). For a detailed discussion of this experimental measure of the C=C bond polarizability see C. K. Ingold, “Structure and Mechanism in Organic Chemistry,” Cornell University Press, Ithaca, N. Y., 1953, p 119.
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    • 1,1-Dimethoxyethylene undergoes substitution with azodiformates unpublished results
    • 1,1-Dimethoxyethylene undergoes substitution with azodiformates; E. Koerner von Gustorf and D. V. White (1969), unpublished results.
    • (1969)
    • Koerner von Gustorf, E.1    White, D.V.2
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    • to be published, obtained cis-di-i-butyl azodiformate (95+ %) mp 32-34
    • E. Koerner von Gustorf and D. Hess, to be published, obtained cis-di-i-butyl azodiformate (95+ %) mp 32-34.
    • Koerner von Gustorf, E.1    Hess, D.2
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    • Melting points are uncorrected. Ir spectra were taken with a grating spectrometer MH-2, SEM Brilckl, Munich, and with a Beckman IR-12. The nmr spectra (r) were recorded with a Varian A-60A and HA-100; the letter abbreviations used follow: s -singlet, d = doublet, t = triplet, q Å quartet, qui = quintet, o ∗= octet, m ∗ multiplet, b -broad; tetramethylsilane was used as internal standard. Molecular weights were determined cryoscopically or osmometrioally (Mechrolab) in benzene. Indene, DEAD, and DMAD (all supplied by Aldrich) were purified by distillation- Illumination techniques have been described by G. O. Schenck, in Springer-Verlag, Heidelberg
    • Melting points are uncorrected. Ir spectra were taken with a grating spectrometer MH-2, SEM Brilckl, Munich, and with a Beckman IR-12. The nmr spectra (r) were recorded with a Varian A-60A and HA-100; the letter abbreviations used follow: s -singlet, d = doublet, t = triplet, q Å quartet, qui = quintet, o ∗= octet, m ∗ multiplet, b -broad; tetramethylsilane was used as internal standard. Molecular weights were determined cryoscopically or osmometrioally (Mechrolab) in benzene. Indene, DEAD, and DMAD (all supplied by Aldrich) were purified by distillation- Illumination techniques have been described by G. O. Schenck, in A. Schönberg “Präparative Organische Photochemie,” Springer-Verlag, Heidelberg, 1958, p 210.
    • (1958) Präparative Organische Photochemie , pp. 210
    • Schönberg, A.1
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    • We extracted the orude ethoxyacetylene from the reaction mixture with n-butyl ether instead of distilling it at 100°
    • E. R. H. Jones, G. Eglinton, M. C. Whiting, and B. L. Shaw, Org. Syn., 34, 46 (1954). We extracted the orude ethoxyacetylene from the reaction mixture with n-butyl ether instead of distilling it at 100°.
    • (1954) Org. Syn. , vol.34 , pp. 46
    • Jones, E.R.H.1    Eglinton, G.2    Whiting, M.C.3    Shaw, B.L.4


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