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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 9-10
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Original Articles

A Convenient Preparation of Benzylic Homopropargylic Alcohols Via Allenyllithium Reagents

Pages 1705-1711 | Received 09 Jan 1989, Published online: 24 Oct 2006

References

  • Brandsma , L. 1971 . Preparative acetylenic chemistry , New York : Elsevier Publishing Company . Amsterdam, London
  • Rutledge , T. F. 1968 . Acetylenic compounds - Preparation and substitution reactions , New York, Amsterdam, London : Rheinhold Book Corp. . N
  • Brandsma , L. and Verkruijsse , H. D. 1981 . Synthesis of acetylenes, allenes and cumulenes , Amsterdam : Elsevier Scientific Publishing Company .
  • Wotiz , J. H. 1969 . “ Chapter 7 ” . In Chemistry of acetylene , 365 New York : Marcel Dekker .
  • Rutledge , T. F. 1969 . Acetylenes and allenes , New York, Amsterdam, London : Rheinhold Book Corp . part II: Acetylene-allene isomerization.
  • Moreau , J. L. 1980 . The chemistry of ketenes, allenes, and related compounds , Edited by: Patai , S. 363 New York : John Wiley and Sons .
  • Michelot , D. 1976 . Ph.D. Dissertation University of Paris ,
  • Linstrumelle , G. and Michelot , D. 1975 . J. Chem. Soc. (Chem. Comm.) , : 561
  • Michelot , D. and Linstrumelle , G. 1976 . Tetrahedron Lett. , : 275
  • Michelot , D. , Clinet , J. C. and Linstrumelle , G. 1982 . Synth. Commun. , 12 : 739
  • Clinet , J. C. and Linstrumelle , G. 1981 . Synthesis , : 875 This procedure has been already explored with a limited number of carbonyl compounds, see: ref. 7, andHooz, J., Calzada, J. and McMaster, D., Tetrahedron Lett., 1985, 26, 271.
  • Creary , X. 1977 . J. Am. Chem. Soc. , 99 : 7632 Under diverse experimental procedures the substituted allenyllithium reagent might lead mainly to the allenyl alcohol. The occurrence of allenic alcohols versus to homopropargylic ones still remains unclear; among the different explanations, it has been hypothesized that the ratio of the different products is dependent upon many factors including the degree of substitution in the organometallic reagents and the steric hindrance of the carbonylic electrophile. Aldehydes would produce preferentially homopropargylic alcohols, while hindered ketones more of the allenic alcohols; it has been observed that aromatic substrates give more easily homopropargylic alcohols than their aliphatic homologues, see:

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