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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 6
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Original Articles

Alkylation-Reduction of Carbonyl Systems. V. The Selective Synthesis of o-Tolylphenylmethanol and o-Tolylphenylmethane by Phenylation-Reduction of Benzocyclobutenone

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Pages 441-444 | Received 14 Jul 1975, Published online: 06 Dec 2006

References

  • Hall , S. S. and McEnroe , F. J. 1975 . J. Org. Chem. , 40 : 271
  • Hall , S. S. 1973 . J. Org. Chem. , 38 : 1738
  • Hall , S. S. and Lipsky , S. D. 1973 . J. Org. Chem. , 38 : 1735
  • Hall , S. S. and Lipsky , S. D. 1971 . J. Chem. Soc., Chem. Commun. , : 1242
  • Hall , S. S. and Lipsky , S. D. in press . Org. Synth. ,
  • Smith , M. 1968 . Reduction , Edited by: Augustine , R. L. 105 New York, N.Y. : Marcel Dekker . Sodium benzoate was first suggested as a quenching agent by, apparently based on relative rate studies of A. P. Krapcho and A. A. Bothner-By, J. Amer. Chem. Soc., 81, 3658 (1959)
  • Hall , S. S. , Lipsky , S. D. and Small , G. H. 1971 . Tetrahedron Lett. , : 1853
  • Hall , S. S. , Lipsky , S. D. , McEnroe , F. J. and Bartels , A. P. 1971 . J. Org. Chem. , 36 : 2588
  • Spangler , R. J. and Kim , J. H. 1972 . Tetrahedron Lett. , : 1249
  • Hedaya , E. and Kent , M. E. 1970 . J. Amer. Chem. Soc. , 92 : 2149
  • Cava , M. P. , Mangold , D. and Muth , K. 1964 . J. Org. Chem. , 29 : 2947
  • Cava , M. P. and Muth , K. 1960 . J. Amer. Chem. Soc. , 82 : 652
  • The experimental procedures and techniques used here have been previously described in reference 1a
  • Mass spectrum m/e (relative intensity) 198 (M+, 39), 183(22), 180(56), 165(20), 119(100), 105(86), 93(44), 92(63), 91(62), and 77(62). Anal. Calcd for C14H14O: C, 84.81; H, 7.12. Found: C, 84.89; H, 7.12
  • Mass spectrum m/e (relative intensity) 182 (M+, 81), 167(100), 104(48), 91(33), and 77(24). Anal. Calcd for C14H14: C, 92.26; H, 7.74. Found: C, 92.23; H, 7.71
  • Horner , L. , Subramaniam , P. V. and Eiben , K. 1968 . Justus Liebigs Ann. Chem. , 714 : 91
  • The intermediacy of a benzophenone derivative which is reduced by lithium-ammonia to 3 can be excluded since the reduction of benzophenone to the corresponding alkoxide in lithium-ammonia is known to be very slow. See reference 3b

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