Phenyl(trimethylsilyl)ketene. Some ketene reactions with diazomethane

作者: William T Brady , Theresa C Cheng

DOI: 10.1016/S0022-328X(00)81435-7

关键词: ChemistryZincCycloadditionChlorideTrimethylsilylReactivity (chemistry)KeteneOrganic chemistryDiazomethaneHalogenation

摘要: Abstract Phenyl(trimethylsilyl)ketene was prepared by the zinc dehalogenation of phenyl(trimethylsilyl)bromoacetyl chloride. This ketene parallels tirmethylsilylketene in stabibility and lack reactivity cycloaddition reactions. The reaction phenyl(ethyl)-, phenyl(trimethylsilyl)- trimethylsilylketenes with diazomethane at −78°C is described. Only 2 1 cycloadducts, cyclobutanones, could be isolated.

参考文章(7)
G.S. Zaitseva, G.S. Bogdanova, Yu.I. Baukov, I.F. Lutsenko, Silylated and germylated cyclopropanones Journal of Organometallic Chemistry. ,vol. 121, ,(1976) , 10.1016/S0022-328X(00)80778-0
Ronald A. Ruden, Trimethylsilylketene. Acylation and olefination reactions Journal of Organic Chemistry. ,vol. 39, pp. 3607- 3608 ,(1974) , 10.1021/JO00938A041
William T. Brady, Edwin D. Dorsey, Fred H. Parry, Halogenated ketenes. IX. Ketene carbodiimide cycloadditions The Journal of Organic Chemistry. ,vol. 34, pp. 2846- 2848 ,(1969) , 10.1021/JO01262A011
P. Lipp, J. Buchkremer, H. Seeles, Studien in der Cyclopropan-Reihe. Cyclo-propanon Justus Liebig's Annalen der Chemie. ,vol. 499, pp. 1- 25 ,(1932) , 10.1002/JLAC.19324990102
Henry. Gilman, Frederick J. Marshall, Cleavage of Some Organosilanes by Hydrogen Chloride Journal of the American Chemical Society. ,vol. 71, pp. 2066- 2069 ,(1949) , 10.1021/JA01174A049
Willis B. Hammond, Nicholas J. Turro, Cyclopropanones. III. 2,2-Dimethylcyclopropanone Journal of the American Chemical Society. ,vol. 88, pp. 2880- 2881 ,(1966) , 10.1021/JA00964A066