A Study on the β-Elimination Reaction from N-[2-( p -nitrophenyl)ethyl]quinuclidinium and 2-( p -nitrophenyl)ethyl bromide induced by amines in dimethylsulfoxide with formation of p -nitrostyrene †
Free accessOtherFirst published online February, 2000
A Study on the β-Elimination Reaction from N-[2-( p -nitrophenyl)ethyl]quinuclidinium and 2-( p -nitrophenyl)ethyl bromide induced by amines in dimethylsulfoxide with formation of p -nitrostyrene †
Second order rate constants kE M−1 s−1 for the β-elimination reaction from N-[2-(p-nitrophenyl)ethyl]quinuclidinium and 2-(p-nitrophenyl)ethyl bromide induced by amines of different structure in dimethylsulfoxide at 50 °C have been measured. Application of the Brønsted equation shows a similar behaviour of the two substrates, with values of β = 0.649 and 0.584 respectively.
References
1.
SaundersW.H., and CokerillA. F., Mechanism of Elimination ReactionsWiley Interscience, New York, 1973
2.
BaciocchiE., The Chemistry of Halides, Pseudo Halides and Azides Supplement D, PataiS., and RappoportZ. (eds), Wiley, Chichester, 1983.
3.
GandlerJ.R., The Chemistry of Double-Bonded Functional Groups, PataiS. (ed.) Wiley, New York1989
4.
AlunniS., and JencksW. P., J. Am. Chem. Soc., 1980, 102, 2052.
5.
KeeffeJ.R., and JencksW. P., J. Am. Chem. Soc., 1983, 105, 265.
6.
GandlerJ.R., JencksW. P., J. Am. Chem. Soc., 1982, 104, 1937.
7.
BruiceP.Y., J. Am Chem. Soc., 1984, 106, 5959.
8.
BernasconiC.F., and BunnellR. D., Isr. J. Chem., 1985, 26, 420.
9.
BuntingJ.W., and StefanidisD., J. Am. Chem. Soc., 1990, 112, 779.
10.
BrønstedJ.N., and PedersenK., Z. Phys. Chem., 1924, 108, 185.
11.
KresgeA.J., Chem. Soc. Rev., 1973, 2, 475.
12.
ChoB.R., LeeS. J., and KimY. K., J. Org. Chem., 1995, 60, 2072.
13.
BernasconiC.F., Acc. Chem. Res., 1987, 20, 301.
14.
MarcusR.A., J. Phys. Chem.1968, 72, 891.
15.
KolthoffI.M., ChantooniM. K.Jr., and BhowmikS., J. Am. Chem. Soc., 1968, 90, 23.
16.
BernasconiC.F., Acc. Chem. Res., 1992, 9, 25.
17.
BenoitR.L., LefevbreD., and FrèchetteM., Can J. Chem.1987, 65, 996.
18.
BenoitR.L., BouletD., SeguinL., and FrèchetteM., Can J. Chem., 1985, 63, 1228.
