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Volumn 95, Issue 10, 1973, Pages 3284-3289

Peroxy Acid Oxidation of Cycloalkynes and the Decomposition of 2-Diazocycloalkanones

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EID: 2242452554     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00791a035     Document Type: Article
Times cited : (36)

References (68)
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  • 2
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  • 3
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    • Despite several incorrect claims to the contrary in the earlier literature, oxirenes have nevrr been isolated or detected. For a summary, see
    • Despite several incorrect claims to the contrary in the earlier literature, oxirenes have nevrr been isolated or detected. For a summary, see V. Franzen, JustusLiebigs Ann. Chem., 614, 31 (1958).
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  • 8
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    • NOTE ADDED IN PROOF. After submission of our original manuscript two papers recently appeared on the mechanism of the Wolff rearrangement
    • NOTE ADDED IN PROOF. After submission of our original manuscript two papers recently appeared on the mechanism of the Wolff rearrangement: J. Fenwick, G. Frater, K. Ogi, and O. P. Strausz, J. Amer. Chem. Soc., 95, 124 (1973);
    • (1973) J. Amer. Chem. Soc. , vol.95 , pp. 124
    • Fenwick, J.1    Frater, G.2    Ogi, K.3    Strausz, O.P.4
  • 10
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    • These authors question the participation of oxirenes in the photochemical Wolff rearrangement of a-diazo ketones on the basis of evidence which supports the intervention of oxirene in the photolysis of ketene
    • R. L. Russell and F. S. Rowland, J. Amer. Chem. Soc., 92, 7508 (1970). These authors question the participation of oxirenes in the photochemical Wolff rearrangement of a-diazo ketones on the basis of evidence which supports the intervention of oxirene in the photolysis of ketene.
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    • and previous papers
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    • We are indebted to Professor Gutsche for a gift of authentic 9
    • D. M. Bailey, J. E. Bowers, and C. D. Gutsche, J. Org. Chem., 28, 610 (1963). We are indebted to Professor Gutsche for a gift of authentic 9.
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  • 28
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    • We are grateful to Professor House for providing us with an authentic sample of 10 and its trans isomer
    • H. O. House and G. H. Rasmussen, J. Org. Chem., 28, 31 (1963). We are grateful to Professor House for providing us with an authentic sample of 10 and its trans isomer.
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    • House, H.O.1    Rasmussen, G.H.2
  • 37
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    • We are grateful to Professor Carlson for providing us with an authentic sample of 16 as well as infrared and nmr data of both 16 and its trans isomer
    • R. G. Carlson and J. H. Bateman, J. Org. Chem., 32, 1608 (1967). We are grateful to Professor Carlson for providing us with an authentic sample of 16 as well as infrared and nmr data of both 16 and its trans isomer.
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    • For a review of transannular carbene reactions in medium-sized rings, see
    • For a review of transannular carbene reactions in medium-sized rings, see A. C. Cope, M. M. Martin, and M. A. McKervey, Quart. Rev., CAem. Soc, 20, 119 (1966).
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    • Cope, A.C.1    Martin, M.M.2    McKervey, M.A.3
  • 41
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    • We are grateful to Professor C. S. Foote for kindly sending us an authentic sample of 22
    • C. D. Poulter, E. C. Friedrich, and S. Winstein, J. Amer. Chem. Soc, 91, 6892 (1969). We are grateful to Professor C. S. Foote for kindly sending us an authentic sample of 22.
    • (1969) J. Amer. Chem. Soc , vol.91 , pp. 6892
    • Poulter, C.D.1    Friedrich, E.C.2    Winstein, S.3
  • 45
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    • See, and references cited therein
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    • Gutsche, C.D.1    Baum, J.W.2
  • 49
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    • Carbenes, Nitrenes, and Arynes
    • Appleton-Century-Crofts, New York, N. Y.
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    • (1969) , pp. 77
    • Gilchrist, T.L.1    Rees, C.W.2
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    • Carbene Chemistry
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    • 30b of cyclooctanone rather than via the acyloin condensation of dimethyl suberate
    • 30b of cyclooctanone rather than via the acyloin condensation of dimethyl suberate.
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    • sob was adapted for the synthesis of 1, 2-cyclododecanedione
    • sob was adapted for the synthesis of 1, 2-cyclododecanedione.
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  • 68
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    • We wish to thank Dr. Negishi for supplying us with an authentic sample of -ans-bicyclo[5. 3. 0]decan-8-one
    • H. C. Brown and E. Negishi, Chem. Commun., 594 (1968). We wish to thank Dr. Negishi for supplying us with an authentic sample of -ans-bicyclo[5. 3. 0]decan-8-one.
    • (1968) Chem. Commun. , pp. 594
    • Brown, H.C.1    Negishi, E.2


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