Wittig Reaction of a Series of Diazodiketones: Synthesis and Structure of Fluorine-Containing Vinyldiazoketones

Abstract

Reaction of (alkyloxycarbonyl)- and (benzoyl)-methyl­enetriphenylphosphoranes with fluorine-containing diazodiketones leads to olefination of the perfluoroacyl carbonyl group and formation of fluorinated vinyldiazoketones. The analogous reaction with non-fluorinated diazodiketones does not proceed under the same conditions. The resulting fluorine-containing vinyldiazoketones have an E-configuration regardless of the nature and size of the substituents.

Key words

aliphatic diazo compounds - Wittig reaction - fluorine-containing vinyldiazoketones - 1,3-diketones - diazo transfer reaction

References

• 1a Murphy PJ. Brennan J. Chem. Soc. Rev.  1988,  17:  1 
• 1b Murphy PJ. Lee SE. J. Chem. Soc., Perkin Trans. 1  1999,  3049 
• 2 Maercker A. Org. React.  1965,  14:  270 
• 3 Guillaume M. Janousek Z. Viehe HG. Synthesis  1995,  920 
• 4 Capuano L. Drescher S. Volker H. Liebigs Ann. Chem.  1991,  331 
• 5 Wang Y. Zhu S. Zhu G. Huang Q. Tetrahedron  2001,  57:  7337 
• 6a Davies HML. Clark T. Smith HD. J. Org. Chem.  1991,  56:  3817 
• 6b Davies HML. Antoulinakis EG. Org. React.  2001,  57:  326 
• 7 Doyle MP. Yan M. Hu W. Gronenberg LS. J. Am. Chem. Soc.  2003,  125:  4692 
• 8a Regitz M. Maas G. Diazo Compounds. Properties and Synthesis   Academic Press; New York: 1986.  p.326 
• 8b Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   Wiley; New York: 1998.  p.9 
• 9a Doyle MP. Dorrow RL. Terpstra JW. Rodenhouse RA. J. Org. Chem.  1985,  50:  1663 
• 9b Nikolaev VA. Utkin PYu. Korobitsyna IK. Zh. Org. Khim.  1989,  25:  1176 
• 10 Nikolaev VA. Kantin GP. Utkin PYu. Zh. Org. Khim.  1994,  30:  1292 
• 11a Alloum AB. Villemin D. Synth. Commun.  1989,  19:  2567 
• 11b Popik VV. Korneev SM. Nikolaev VA. Korobitsyna IK. Synthesis  1991,  195 
• 12 Galiullina SV. Zakharova VM. Kantin GP. Nikolaev VA. Zh. Org. Khim.  2005,  in press 
• 13a Kaplan F. Meloy GK. J. Am. Chem. Soc.  1966,  88:  950 
• 13b Lauer W. Krause V. Wengenroth H. Meier H. Chem. Ber.  1988,  121:  465 
• 13c Nikolaev VA. Popik VV. Korobitsyna IK. Zh. Org. Khim.  1991,  27:  505 
• 14 Davies HML. Clark DM. Smith TK. Tetrahedron Lett.  1988,  26:  5659 
• 15 Eguchi T. Aoyama T. Kakinuma K. Tetrahedron Lett.  1992,  33:  5545 
• 16 Nägele U. Hanack M. Liebigs Ann. Chem.  1989,  847 
• 17 Johnson A. Ylid Chemistry   Academic Press; New York: 1966.  p.400