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

Valerija M. Zakharova; Lothar Hennig; Valerij A. Nikolaev

doi:10.1055/s-2005-872180

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Synthesis 2005(17): 2871-2874
DOI: 10.1055/s-2005-872180

PAPER

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

Valerija M. Zakharova^a, Lothar Hennig^b, Valerij A. Nikolaev*^a
^a St. Petersburg State University, Department of Organic Chemistry, University pr. 26, 198504 St. Petersburg, Russia
e-Mail: vnikola@VN6646.spb.edu;
^b Universität Leipzig, Institut für Organische Chemie, Johannisallee 29, 04103 Leipzig, Germany
e-Mail: hennig@organik.chemie.uni-leipzig.de;

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Publication History

Received 31 December 2004
Publication Date:
17 August 2005 (online)

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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

Crossref Google Scholar
1b Murphy PJ. Lee SE. J. Chem. Soc., Perkin Trans. 1 1999, 3049

Crossref Google Scholar
2 Maercker A. Org. React. 1965, 14: 270

Google Scholar
3 Guillaume M. Janousek Z. Viehe HG. Synthesis 1995, 920

Article in Thieme Connect Google Scholar
4 Capuano L. Drescher S. Volker H. Liebigs Ann. Chem. 1991, 331

Google Scholar
5 Wang Y. Zhu S. Zhu G. Huang Q. Tetrahedron 2001, 57: 7337

Crossref Google Scholar
6a Davies HML. Clark T. Smith HD. J. Org. Chem. 1991, 56: 3817

Google Scholar
6b Davies HML. Antoulinakis EG. Org. React. 2001, 57: 326

Google Scholar
7 Doyle MP. Yan M. Hu W. Gronenberg LS. J. Am. Chem. Soc. 2003, 125: 4692

Google Scholar
8a Regitz M. Maas G. Diazo Compounds. Properties and Synthesis Academic Press; New York: 1986. p.326

Google Scholar
8b Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds Wiley; New York: 1998. p.9

Google Scholar
9a Doyle MP. Dorrow RL. Terpstra JW. Rodenhouse RA. J. Org. Chem. 1985, 50: 1663

Google Scholar
9b Nikolaev VA. Utkin PYu. Korobitsyna IK. Zh. Org. Khim. 1989, 25: 1176

Google Scholar
10 Nikolaev VA. Kantin GP. Utkin PYu. Zh. Org. Khim. 1994, 30: 1292

Google Scholar
11a Alloum AB. Villemin D. Synth. Commun. 1989, 19: 2567

Article in Thieme Connect Google Scholar
11b Popik VV. Korneev SM. Nikolaev VA. Korobitsyna IK. Synthesis 1991, 195

Article in Thieme Connect Google Scholar
12 Galiullina SV. Zakharova VM. Kantin GP. Nikolaev VA. Zh. Org. Khim. 2005, in press

Google Scholar
13a Kaplan F. Meloy GK. J. Am. Chem. Soc. 1966, 88: 950

Google Scholar
13b Lauer W. Krause V. Wengenroth H. Meier H. Chem. Ber. 1988, 121: 465

Google Scholar
13c Nikolaev VA. Popik VV. Korobitsyna IK. Zh. Org. Khim. 1991, 27: 505

Google Scholar
14 Davies HML. Clark DM. Smith TK. Tetrahedron Lett. 1988, 26: 5659

Google Scholar
15 Eguchi T. Aoyama T. Kakinuma K. Tetrahedron Lett. 1992, 33: 5545

Crossref Google Scholar
16 Nägele U. Hanack M. Liebigs Ann. Chem. 1989, 847

Google Scholar
17 Johnson A. Ylid Chemistry Academic Press; New York: 1966. p.400

Google Scholar