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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 16-17
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Original Articles

A Convenient Synthesis of (R)-(+)-Perillaldehyde

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Pages 1905-1911 | Published online: 05 Dec 2006

References

  • 1987–1989 . Fellow of the Alfred P. Sloan Foundation
  • S)-(-)-Perillaldehyde is available from Aldrich Chemical Co. The racemate is available from Tokyo Kasei, Inc.
  • Both enantiomers of perillaldehyde had been offered for sale by Research Organics, Inc., Belleville, N. J. Our repeated inquiries to this company were not answered. Professor David B. Collum (Cornell University) supplied us with a sample purchased from Research Organics as (R)-(+)-perillaldehyde. This material was, in fact, the levorotatory (S)-isomer, so it remains unclear whether (R)-(+)-perillaldehyde has ever been available from a commercial source
  • Semmler , F. W. and Zaar , B. 1911 . Chem. Ber. , 44 : 815
  • Schmidt , H. 1950 . Chem. Ber. , 83 : 193
  • Barton , D. H. R. , Blair , I. A. and Magnus , P. D. 1972 . J. Chem. Soc., Perkin Trans. I , : 614
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  • Several schemes for isomerizing (+)-alpha-pinene to (+)-beta-pinene have been reported, but none are convenient on a large scale:
  • Harwood , L. M. and Julia , M. 1980 . Synthesis , : 456
  • Midland , M. M. , Petre , J. E. , Zderic , S. A. and Kazubski , A. 1982 . J. Am. Chem. Soc. , 104 : 528
  • Deleris , G. , Kowalski , J. , Dunogues , J. and Calas , R. 1977 . Tetrahedron Lett. , : 4211
  • Both enantiomers of limonene oxide are available from Aldrich Chemical Co.
  • Mosset , P. , Manna , S. , Viala , J. and Falck , J. R. 1986 . Tetrahedron Lett. , 299
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  • Sugihara , H. , Tanikaga , R. and Kaji , A. 1978 . Synthesis , : 881

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