luis rodriguez | Universidad Cesar Vallejo Trujillo (original) (raw)

Papers by luis rodriguez

Advanced Synthesis & Catalysis, 2002

A study for determining the scope and limitations of a procedure for synthesising ethylene acetal... more A study for determining the scope and limitations of a procedure for synthesising ethylene acetals from haloketones is presented. The method uses 1,2-bis(trimethylsilyloxy)ethane, BTSE, as reagent and Nafion ¾-TMS as catalyst. Two procedures have been tested: (A) stoichiometric amounts of the haloketone and BTSE and a catalytic amount of Nafion ¾-TMS were heated to reflux in chloroform solution, and (B) stoichiometric amounts of the reactants and a catalytic amount of Nafion ¾-TMS were heated to 90 ± 100 8C in the absence of solvent. The following ketones have been tested: 2-bromo-1-phenyl-1ethanone, 2-bromo-cyclopentenone, 3-bromo-3-methyl-2butanone, 3-chloro-3-methyl-2-butanone, 1-bromo-3,3-dimethyl-2-butanone, 1-chloro-3,3-dimethyl-2-butanone, 2-bromocyclohexanone, 2-chloro-1-cyclohexyl-1-ethanone, 1,1-dibromo-3,3-dimethyl-2-butanone, 1,3-dibromo-3-methyl-2-butanone, 1,3-dibromo-2-butanone, 1,3-dibromo-2propanone, 2-chloro-1-phenyl-1-ethanone, and endo-2-bromocamphor. Yields were in the range 57 ± 100% with the exceptions of endo-2-bromocamphor which afforded < 10% yield and the dibromoketones 1,1-dibromo-3,3-dimethyl-2butanone and 1,3-dibromo-3-methyl-2-butanone for which the method failed. Factors determining the scope and limitations are briefly discussed. Full experimental details and spectroscopic data of the acetals are given.

Advanced Synthesis & Catalysis, 2002

A study for determining the scope and limitations of a procedure for synthesising ethylene acetal... more A study for determining the scope and limitations of a procedure for synthesising ethylene acetals from haloketones is presented. The method uses 1,2-bis(trimethylsilyloxy)ethane, BTSE, as reagent and Nafion ¾-TMS as catalyst. Two procedures have been tested: (A) stoichiometric amounts of the haloketone and BTSE and a catalytic amount of Nafion ¾-TMS were heated to reflux in chloroform solution, and (B) stoichiometric amounts of the reactants and a catalytic amount of Nafion ¾-TMS were heated to 90 ± 100 8C in the absence of solvent. The following ketones have been tested: 2-bromo-1-phenyl-1ethanone, 2-bromo-cyclopentenone, 3-bromo-3-methyl-2butanone, 3-chloro-3-methyl-2-butanone, 1-bromo-3,3-dimethyl-2-butanone, 1-chloro-3,3-dimethyl-2-butanone, 2-bromocyclohexanone, 2-chloro-1-cyclohexyl-1-ethanone, 1,1-dibromo-3,3-dimethyl-2-butanone, 1,3-dibromo-3-methyl-2-butanone, 1,3-dibromo-2-butanone, 1,3-dibromo-2propanone, 2-chloro-1-phenyl-1-ethanone, and endo-2-bromocamphor. Yields were in the range 57 ± 100% with the exceptions of endo-2-bromocamphor which afforded < 10% yield and the dibromoketones 1,1-dibromo-3,3-dimethyl-2butanone and 1,3-dibromo-3-methyl-2-butanone for which the method failed. Factors determining the scope and limitations are briefly discussed. Full experimental details and spectroscopic data of the acetals are given.