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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 7
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Original Articles

A Convenient Procedure for the Reduction of Diarylmethanols with Dichlorodimethylsilane/Sodium Iodide

Pages 741-749 | Published online: 19 Dec 2006

References

  • Ando , W. and Ikeno , M. Tetrahedron Lett. , 1979 4941 Examples of this reduction include: (CH3)2Sil2
  • Hartung , W. H. and Simonoff , R. 1953 . Hydrogenolysis of Benzyl Groups Attached to Oxygen, Nitrogen or Sulfur , Vol. VII , 263 Org. Reactions . H2, Pd:
  • Kursanov , D. N. , Parnes , Z. N. and Loim , N. M. 1974 . Synthesis , : 633 Carey, F. A.; Tremper, H. S. J. Org. Chem. 1969, 34, 4 Et3SiH, CF3CO2H
  • Gribble , G. W. , Leese , R. M. and Evans , B. E. 1977 . Synthesis , : 172 NaBH4, CF3CO2H
  • Olah , G. A. and Prakash , G. K. S. 1978 . Synthesis , : 397 Cyclohexene, Pd-C, AlCl3
  • Small , G. H. , Minella , A. E. and Hall , S. S. 1975 . J. Org. Chem. , 40 : 3151 Li-NH3, NH4Cl
  • Anderson , H. H. 1951 . J. Am. Chem. Soc. , 73 : 2351 For the preparation of diiododimethylsilane, see
  • Van den Berghe , E. V. and Van der Kelen , G. P. 1973 . J. Organomet. Chem. , 59 : 175
  • Durig , J. R. and Hawley , C. W. 1973 . J. Chem. Phys. , 58 : 237
  • Olah , G. A. , Narang , S. C. , Gupta , B. G. B. and Malhotra , R. 1979 . J. Org. Chem. , 44 : 1247 Olah, G. A.; Husain, A.; Singh, B. P.; Mehrotra, A. K. J. Org. Chem. 1983, 48, 3667 Although chlorotrimethylsilane/Nal and trichloromethylsilane/Nal have been employed as the iodosilane equivalents, the reagent formed from dichlorodimethylsilane and sodium iodide has not, to our knowledge been examined. See for example
  • Morita , T. , Yoshida , S. , Okamoto , Y. and Sakurai , H. 1979 . Synthesis , : 379
  • The reaction of benzhydrol with dichlorodimethylsilane in the absence of sodium iodide produced a 31% yield of benzhydryl chloride, along with recovered starting material. .
  • If the reduction of alcohol 1 is carried out at room temperature, one obtains a 2:1 mixture of product 2 and fluorenes 3 and 4 in 48% combined yield.

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