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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 1
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Original Articles

Novel Preparation of Cyanophenylcyclopropanes Via Cyanophenylcarbene

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Pages 21-25 | Published online: 05 Dec 2006

References

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  • Petrellis , P. C. , Dietrich , H. , Meyer , E. and Griffin , G. W. 1967 . J. Am. Chem. Soc. , 89 : 1967
  • Petrellis , P. C. and Griffin , G. W. 1967 . Chem. Commun. , : 691
  • Petrellis , P. C. and Griffin , G. W. 1968 . Chem. Commun. , : 1099
  • Cox , D. P. , Moss , R. A. , Terpinski , J. , Włostowska , J. , Moss , R. A. , Guo , W. and Chang , M. J. 1982 . Chem. Commun. , : 432 submitted for publication. See also
  • Graham , W. H. 1965 . J. Am. Chem. Soc. , 87 : 4396
  • Kobler , H. , Munz , R. , Al Gasser , G. and Simchen , G. 1978 . Annalen , : 1937 The reagent was dried overnight at 50°C/≃3 mm-Hg
  • The photolytic method results in 5–12% higher yields, and is preferable
  • Liu , M. T. H. 1982 . Chem. Soc. Rev. , 11 : 127
  • Wasserman , E. , Kuck , V. , Trozzolo , A. M. and Wasserman , E. 1975 . Carbenes , Edited by: Moss , R. A. and Jones , M. Jr. Vol. II , 185ff New York : Wiley . cited in cf., Table 1, p. 193
  • The adducts are thermally stable to the gc analytical conditions
  • Closs , G. L. and Moss , R. A. 1964 . J. Am. Chem. Soc. , 86 : 4042 Configurations were determined by nmr,2a assigning the high field cyclopropyl methyl resonances to the syn-Ph (anti-CN) isomer; cf.
  • The reaction mixture underwent a series of color changes: light yellow, dirty green, yellow, orange, red-orange

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