Organometallics: (I) Synthesis of a macrocyclic complex praeseodymium and (II ) effect of wilkinson's catalyst on the cleavage of cyclohexene oxide by borane

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Title: Organometallics: (I) Synthesis of a macrocyclic complex praeseodymium and (II ) effect of wilkinson's catalyst on the cleavage of cyclohexene oxide by borane
Author: Ruth, Carolyn
Abstract: (I) The template synthesis and characterization of the complex of praeseodymium acetate from 2,6-diacetylpyridine and orthophenylenediamine was attempted. The attempted synthesis produced a green precipitate with a high melting point and poor solubility in organic solvents, unlikely characteristics for compound 1 seen on the page. This project was set aside due to the apparent failure to produce the desired compound. (II) The effect of Wilkinson's catalyst on the treatment of cyclohexene oxide with borane-THF at 72 for 5 1/2 hours was also investigated. Oxidation of the organoborane formed by both the catalyzed and uncatalyzed reactions produced cyclohexanol. Another significant product was one which, according to GC-MS, had a molecular weight of 172. This product was not completely identified. Studies of the progress of both the catalyzed and uncatalyzed reactions were conducted using TLC. TLC showed no evidence of the starting material, cyclohexene oxide, after 30 minutes of reflux. No change in the product mixture measured by TLC occurred after 30 minutes for the catalyzed reaction and after 60 minutes for the uncatalyzed reaction, indicating that the reactions were probably complete at that point.
Record URI: http://hdl.handle.net/1850/12132
Date: 1993-08-14

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