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Selective Ring-opening of Epoxy Ketones with Hantzsch HEH and Application of Hypervalent Iodine in Organic Synthesis

Author: DuanYiQin
Tutor: FuXiangZuo;MuRuiZhu
School: Southwestern University
Course: Organic Chemistry
Keywords: Hans ester Iodine phenone Iodosobenzene Open-loop Acetyl oxidation
CLC: O621.3
Type: Master's thesis
Year: 2010
Downloads: 54
Quote: 0
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Abstract


Based on the Hans ester as many advantages the hydrogen source provider as well as organic hypervalent iodine reagents , used in organic synthesis , carried out the experiments of the following three systems : 1 . Hans ester HEH thermal reaction conditions epoxyketone selective ring opening reaction is carried out on the reaction feasibility exploration, and respectively HEH oxidative aromatization product , the reaction temperature , the relative amounts of the reactants and the catalyst , solvent , air and water in the presence of influence on the reaction . discussed , so as to arrive at the Jiaoyou reaction conditions , yield up to 99% . Reaction without metal catalyst , thus avoiding the commonly used metal catalyst on the environment caused by pollution , the synthesis has a green , mild conditions , easy to operate, good selectivity and high yield characteristics . Iodine acyloxy benzene (IB) Oxidative Aromatization of Hans ester 1,4 - dihydropyridine (1,4-DHPs) derivative respectively solvents , additives , temperature , iodine, acyloxy benzene (IB) of the relative amount of the reaction the impact of the discussion , so as to arrive in Jiaoyou reaction conditions , the highest yield of up to 99% . The reaction using organic hypervalent iodine, and without the catalyst can be performed under mild conditions , easy to operate . Iodosobenzene acetyl oxide on the bit - substituted phenethyl ketone using iodosobenzene acetyl oxidation of para- substituted acetophenone , respectively, the relative amounts of solvents, water, alkylene iodine acyloxy benzene , catalyst trifluoroacetic boron ether, the influence of temperature on the reaction were discussed , draw the better reaction conditions , the highest yield of up to 86.5% . The reaction acetophenone α- acetyl oxidation of the trivalent iodine in the use of organic hypervalent iodine , mild reaction conditions , easy operation, and good selectivity .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Synthetic organic chemistry
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