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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 5
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Original Articles

Synthesis of Adamantane Derivatives. Xxiii. Facile Photo-Ring-Cleavage of 4-Homoadamantanone to Bicyclo[3.3.1] -Nonan-3 -Endo-Acetate

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Pages 369-373 | Received 28 Aug 1973, Published online: 05 Dec 2006

References

  • Sasaki , T. , Eguchi , S. and Mizutani , M. 1972 . Chemistry Lett. , : 991 Part XXII
  • Turro , N. J. , Dalton , J. C. , Dawes , K. , Farrington , G. , Hautals , R. , Morton , D. , Niemczyk , M. and Schore , N. 1972 . Accounts Chem. Res. , 5 : 92 For a recent review, see
  • Dalton , J. C. , Dawes , K. , Turro , N. J. , Weiss , D. S. , Bartrop , J. A. and Coyle , J. D. 1971 . J. Amer. Chem. Soc. , 93 : 7213 For five and six-membered ketones, see;For type II reactions, see P. J. Wagner, Accounts Chem. Res., 4., 168 (1971)
  • Srinivasan , R. 1959 . J. Amer. Chem. Soc. , 81 : 5541 Photolysis of cycloheptanone is known to afford a complex mixture of products: R. Srinivasan and S. E. Cremer, ibid. 87., 1647 (1965)
  • Anal. Calcd for C13H22O2: C, 74.24;H, 10.54. Found: C, 74.46;H, 10.32
  • Sasaki , T. , Eguchi , S. and Toru , T. 1970 . J. Org. Chem. , 35 : 4109
  • Sasaki , T. , Eguchi , S. and Mizutani , M. 1972 . ibid. , 37 : 3961 For details of this preparation, see
  • Nordlander , J. E. , Wu , F. Y.-H. and Jindal , S. P. 1969 . J. Amer. Chem. Soc. , 91 : 949 P. v. R. Schleyer, E. Funke and S. H. Liggero, ibid. 91., 3965 (1969)
  • Piette , L. H. 1960 . NMR and EPR Spectroscopy 221 Pergamon Press . Although the formation of diradical intermediate is generally accepted by ESR and by epimerization data for acetone and 2,3-dimethylcyclohexanone, no evidence for 1 is available at present. 1 has an exceptionally longer singlet lifetime: p; J. A. Barltrop and J. D. Coyle, Chem. Commun., 1081 (1969); N. J. Turro, C. Lee, N. Schore, J. Barltrop and H. A. J. Carless, J. Amer. Chem. Soc., 95, 3079 (1971)

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