Abstract
Ring substituted α-bromoacetophenones undergo efficient photodecomposition upon ultraviolet irradiation in alcohol solvents. The process involves chain reactions mediated by the ketyl radicals derived by hydrogen abstraction from the alcohols. It is suggested that two chain reactions involving hydrogen and electron transfer may be taking place concurrently. Competitive studies lead to relative rate constants for the reactions of ketyl radicals with ring-substituted α-bromoacetophenones.
Similar content being viewed by others
References
C. Heitner and J.C. Scaiano (Eds.),Photochemistry of Lignocellulosic Materials, American Chemical Society, Washington (1993).
J.C. Scaiano, M.K. Whittlesey, A.B. Berinstain, P.R.L. Malenfant and R.H. Schuler,Chem. Mater.,6, 836 (1994).
G.L. Hug,Optical Spectra of Nonmetallic Inorganic Transient Species in Aqueous Solution, National Bureau of Standards, Washington (1981).
W.G. McGimpsey and J.C. Scaiano,Can. J. Chem.,66, 1474 (1988).
J.C. Scaiano, M. Barra, G. Calabrese and R. Sinta,J. Chem. Soc., Chem. Commun., 1418 (1992).
J.C. Scaiano, M. Barra, M. Krzywinski, R. Sinta and G. Calabrese,J. Am. Chem. Soc.,115, 8340 (1993).
S.E. Stein, J.M. Rukkers and R.L. Brown,NIST Structures and Properties Database and Estimation Program, Ver. 1.1, NIST, U.S. Department of Commerce, Gaithersburg (1991).
S.V. Jovanovic, J. Renaud, A. B. Berinstain and J.C. Scaiano,Can. J. Chem.,73, (1995), in press.
F. Fontana, R.J. Kolt, Y. Huang and D.D.M. Wayner,J. Org. Chem.,59, 4671 (1994).
D. Griller and K.U. Ingold,Acc. Chem. Res.,13, 317 (1980).
G. Brunton, H.C. McBay and K.U. Ingold,J. Am. Chem. Soc.,77, 4447 (1977).
V. Nagarajan and R.W. Fessenden,J. Phys. Chem.,89, 2330 (1985).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Renaud, J., Scaiano, J.C. Chain mechanisms for the dehydro-bromination of ring-substituted α-bromoacetophenones in alcohols. Res. Chem. Intermed. 21, 457–465 (1995). https://doi.org/10.1007/BF03052270
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03052270