An Efficient Procedure for the Mild Oxidative Cleavage of Alkene-3-Ols: Application to the Preparation of 2-Alkoxy-2-(3,4,5-Trimethoxyphenyl)- Acetaldehyde

References

• Tabakoff , B. , Groskopf , W. , Anderson , R. and Alivisatos , S. 1974 . Biochem. Pharmacol. , 23 : 1707
   Google Scholar
• Bronaugh , R. L. and Erwin , V. G. 1973 . J. Neurochem. , 21 : 809
   PubMed Web of Science ®Google Scholar
• Smolen , A. and Anderson , A. D. 1976 . Biochem. Pharmacol. , 25 : 317
   PubMed Web of Science ®Google Scholar
• Tabakoff , B. , Anderson , R. and Alivisatos , S. 1973 . Mol. Pharmacol. , 9 : 428
   PubMed Web of Science ®Google Scholar
• Duncan , R. J. S. and Sourkes , T. L. 1974 . J. Neurochem , 22 : 663
   Google Scholar
• Patzlaff , M. and Barz , W. 1978 . Z. Naturforsch., C = Biosci. , 33C ( 9–10 ) : 675
   Google Scholar
• Tinapp , P. 1981 . Arch. Pharm. (Weinheim, Ger.) , 314 : 512
   Google Scholar
• Lipshutz , B. H. and Pegram , J. J. 1980 . Tetrahedron Lett. , : 3343 For the use of -CH2-OCH2CH2TMS as a protecting group see
   Google Scholar
• Rathke , M. W. and Manis , P. A. 1981 . J. Org. Chem. , 46 : 5348 For the use of -SiMe2OC6H2(t-Bu)3 as a protecting group, see
   Google Scholar
• Ogura , K. and Tsuchihashi , G. 1972 . Tetrahedron Lett. , : 2681 2-oxy-2-aryl acetaldehydes have been prepared by the following
   Google Scholar
• Scolastico , C. , Colombo , L. , Gennari , C. , Guanti , G. and Narisano , E. 1981 . J. Chem. Soc., Perkin Trans. I , : 1278
   Google Scholar
• Bal'on , Y. G. and Shul'man , M. D. 1976 . Zh. Org. Khim. , 12 : 1973
   Google Scholar
• Pine , S. H. and Cheney , J. 1975 . J. Org. Chem. , 40 : 870
   Google Scholar
• The inductive effect of the three methoxy groups must be responsible for stabilizing the negative charge of anion 3. Further support for this type of mechanism was obtained from an experiment in which ether 4b (4, R = CH2OCH2CH2TMS) was treated with n-BuLi in THF at O° C for 15 minutes. The purple anion formed could then be quenched with D2O to obtain a mixture of ether 4b and its mono-deuterated analog at the benzylic carbon.
   Google Scholar
• Sam , D. J. and Simmons , H. F. 1972 . J. Am. Chem. Soc. , 94 : 4024
   Web of Science ®Google Scholar
• van Rheenen , V. , Kelly , R. C. and Cha , D. Y. 1976 . Tetrahedron Lett. , : 1973 The use of a tertiary amine oxide with a catatlyic amount of OsO4 was first reported
   Google Scholar
• Duboudin , F. , Cazeau , Ph. , Moulines , F. and Laporte , O. 1982 . Synthesis. , : 212
   Google Scholar
• All new compounds gave satisfactory 1H-NMR, IR, MS and/or combustion analysis data.
   Google Scholar