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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 2
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Original Articles

Homologation of α,β-Ethylenic Ketones in Substituted β,γ-Ethylenic Ketones Using Phosphoniosilylation

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Pages 185-189 | Published online: 19 Dec 2006

References

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  • Stowell , J. C. and Keith , D. R. 1979 . Synthesis , 132
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  • Torreilles , E. , Fonte , M. and Cristau , H. J. March 1986 . Réunion de la Division Organique de la Société Franĉaise de Chimie Paris
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  • Kozikowski , A. P. and Jung , S. H. 1986 . J. Org. Chem. , 51 : 3400
  • 2 (R1R2C=CHCH2COCH3, Z and E): |R1, R2; 1H NMR ppm|; a °C6H5, H; 2.13 and 2.16 (s. and s., 3H); 3.25 and 3.5 (d. d, J = 5.0 Hz, J = 1.1 Hz and d. d., J = 7, 0 Hz, J = 1.3 Hz, 2H) 5.91 and 6.20 (t. d., J = 11.5 Hz, J = 7.0 Hz and t. d., J = 15.5 Hz, J = 5.0 Hz, 1H) 6.50 and 6.70 (d. d., J = 15.5 Hz, J = 1.1 Hz and d. d., J = 11.5 Hz, J = 1.3 Hz, 1H)|. b °C6H13,H; 0.85 (t. 3H), 1.10–1.30 (m., 8H) 2.10 (s., 3H) 1.95–2.20 (m., 2H) 3.08–3.13 (d., J = 5.0 Hz and d., J = 7 Hz, 2H) 5.40–5.60 (m., 2H)|; c |p-CH3C6H4, H; 2.20 and 2.22 (s. and s., 3H) 2.36 (s., 3H) 3.33 and 3.45 (d., J = 5.0 Hz and d. d., J = 7.5 Hz, J = 1.3 Hz, 2H) 5.90 and 6.10 (t. d., J = 12 Hz, J = 7.5 Hz and t. d., J = 15.0 Hz, J = 5.0 Hz, 1H) 6.40 and 6.66 (d., J = 15.0 Hz and d. d., J = 12.0 Hz, J = 1.1 Hz, 1H)|. d °C6H5, C2H5; 0.97 (t. 3H) 2.05 and 2.2 (s. and s., 3H) 2.53 (q., 2H) 3.05 and 3.33 (d. d., J = 7.0 Hz, J = 1.3 Hz and d. d., J = 7.0 Hz, J = 1.1 Hz, 2H) 5.63 and 5.86 (t. d., J = 7.0 Hz, J = 1.3 Hz and t. d., J = 7.0 Hz, J = 1.1 Hz, 1H)|. e °C6H5, C6H5; 2.00 (s. 3H) 3.20 (d., J = 7.0 Hz, 2H) 6.32 (t., J = 7.0 Hz, 1H)|.
  • In 13C NMR spectrum the carbonyl signal are about δ = 207 ppm. The shifts of allylic carbon shom difference of 6 to 7 ppm upfield, when going from E isomers (δ = 47 ppm) to Z isomers.
  • Brown , H. C. , Bhat , N. G. and Campbell , J. B. Jr. 1986 . J. Org. Chem. , 51 : 3398

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