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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

Nickel (o)-catalyzed Cycloaddition of Ethoxyethyne with Carbon Dioxide to 4,5-diethoxy-α-pyrone

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Pages 1575-1581 | Received 08 Sep 1988, Published online: 24 Oct 2006

References

  • Sneeden , R. P. A. 1982 . Comprehensive Organometallic Chemistry , Edited by: Wilkinson , G. , Stone , F. G. A. and Abel , E. W. Vol. 8 , 225 New York : Pergamon . For recent studies, see reference 3.
  • Walther , D. , Schonberg , H. , Dinjus , E. and Sieler , J. 1987 . J. Organomet. Chem. , 334 : 377
  • Tsuda , T. , Morikawa , S. , Sumiya , R. and Saegusa , T. 1988 . J. Org. Chem. , 53 : 3140 See also: T. Tsuda, R. Sumiya, and T. Saegusa, Synth. Commun., 1987, 17, 147.
  • Inoue , Y. , Itoh , Y. and Hashimoto , H. 1977 . Chem. Lett. , : 855 In this reaction carried out in THF, we observed that another regioisomer, i.e., 4,5-di-n-butyl-α-pyrone was produced together with 4,6-di-n-butyl-α-pyrone in an nearly equal amount.
  • Hoberg , H. , Schaeffer , D. , Burkhart , G. , Kruger , C. and Romao , M. J. 1984 . J. Organomet. Chem. , 266 : 203
  • Ficini , J. and Pouliquen , J. 1971 . J. Am. Chem. Soc. , 93 : 3295 Ynamine is known to react with CO2 at -60 °C without a catalyst to produce allenic amide via 'an initially formed [2+2] cycloadduct. See:
  • Dickstein , J. I. and Miller , S. I. 1978 . The chemistry of the carbon-carbon triple bond , Edited by: Patai , S. 820 New York : John Wiley & Sons . part 2

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