M. B. Supurgibekov et al. / Tetrahedron Letters 52 (2011) 341–345
345
11. (a) Maercker, A. Org. React. 1965, 14, 270–490; (b) Murphy, P. J.; Brennan, J.
Chem. Soc. Rev. 1988, 17, 1–30; (c) Murphy, P. J.; Lee, S. E. J. Chem. Soc., Perkin
Trans. 1 1999, 3049–3066.
analogs possessing cis-functional groups do not undergo 1,5-elec-
trocyclization. On the other hand, phosphazines of vinyldiazocar-
bonyl compounds with
a cis-arrangement of the functional
12. (a) Kolodiazhnyi, O. I. In Phosphorus Ylides. Chemistry and Application in Organic
Synthesis; Wiley-VCH: Weinheim, 1999; (b) Robiette, R.; Richardson, J.;
Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2006, 128, 2394–2409.
13. In the 13C NMR spectra of vinyl acetates H-2b and F-2d only the signals of the
alkoxycarbonyl carbons were present at 170.7 and 170.3 (two isomers of H-2b)
and at 168.9 ppm (for F-2d). In the case of vinylketones H-2c and F-2e only the
signals of the carbon atoms of the acetyl carbonyl groups were observed
(204.7, 204.6, 198.4, 198.2 ppm, associated with four isomers of H-2c) and at
197.8 and 201.0 ppm (related to two isomers of F-2e).
groups on the vinyl bond readily undergo diaza-Wittig reaction
to produce substituted pyridazines, while their counterparts with
trans-configuration remain intact under the same reaction
conditions.
Acknowledgment
14. Two stereoisomers of vinyl acetate H-2b were formed by the Wittig process,
while fluorinated analog F-1d gave only one isomer F-2d. Reaction with
acetylacetone H-1c gave rise to both regioisomers of vinyl ketone H-2c, and
each was represented in the reaction mixture by 2 stereoisomers (altogether 4
isomers in the ratio ꢀ 2:1:7:2 from the signals due to the C2-H protons at 6.24,
6.14, 5.85, 5.73 ppm), whereas the fluorinated analog of acetylacetone F-1e
provided a mixture of two isomers of vinyl ketones F-2e (1:1).
15. (a) Regitz, M.; Maas, G. Diazo Compounds. Properties and Synthesis; Academic
Press: New York, 1986. p 326; (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern
Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New
York, 1998. p 652.
The authors would like to thank Professor G. K. Surya Prakash
(USC, USA) for the kind support and fruitful discussion of the ob-
tained results.
References and notes
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