Triethylamine-promoted Elimination from ( R,R )-PhCHORCHCICO 2 Me (R = MeCO,PhCO,4-MeC 6 H 4,4-MeOC 6 H 4,MeSO 2 and 4-MeC 6 H 4 SO 2 ) in Various Solvents †
Free accessResearch articleFirst published online February, 1999
Triethylamine-promoted Elimination from ( R,R )-PhCHORCHCICO 2 Me (R = MeCO,PhCO,4-MeC 6 H 4,4-MeOC 6 H 4,MeSO 2 and 4-MeC 6 H 4 SO 2 ) in Various Solvents †
The rates and stereochemistry of elimination from a number of (R,R)-PhCHORCHCICO2Me (R = MeCO, PhCO, 4-MeC6H4, 4-MeOC6H4, MeSO2 and 4-MeC6H4SO2) with triethylamine in tetrahydrofuran, acetone, methanol, dimethylformamide and acetonitrile as solvents led to the conclusion that the elimination process occurs through an (E1cB)l mechanism.
References
1.
GarayR. O., and CabaeliroM. C., J. Chem. Soc., Perkin Trans. 2, 1988, 1643.
2.
MarshallD. R., ThomasP. J., and StirlingC. J. M., J. Chem. Soc., Perkin Trans. 2, 1977, 1914; P. J. Thomas and C. J. M. Stirling, J. Chem. Soc., Perkin Trans. 2, 1977, 1909; C. G. Swain and E. C. Jupton, Jr, J. Am. Chem. Soc., 1968, 90, 4328.
3.
BordwellF. G., Acc. Chem. Res., 1972, 5, 374.
4.
GarayR. O., and CabaleiroM. C., J. Chem. Res. (S), 1990, 166.
5.
KamletM. J., and TaftR. W., J. Am. Chem. Soc., 1977, 99, 8325.
6.
HughesE. D., Trans. Faraday Soc., 1941, 37, 763.
7.
SchlosserM., JanG., BirneE., and SicherJ., Helv. Chim. Acta, 1973, 56, 1530; G. Kortün, W. Vogel and K. Andrussov, Pure Appl. Chem. 1960, 1, 190; E. M. Arnett, Prog. Phys. Org. Chem., 1963, 1, 223; D. D. Perrin, Pure Appl. Chem., 1969, 20, 133; H. Cerfontain, A. Koeberg-Telder and C. Kruk, Tetrahedron Lett., 1975, 3639.
