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Development of Synthetic Tools Using Ynol Ether Ionic Chemistry

Development of Synthetic Tools Using Ynol Ether Ionic Chemistry. Benoit Daoust, Département de Chimie-Biologie, Université du Québec à Trois-Rivières, Trois-Rivières, Québec G9A 5H7.

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Development of Synthetic Tools Using Ynol Ether Ionic Chemistry

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  1. Development of Synthetic Tools Using Ynol Ether Ionic Chemistry Benoit Daoust, Département de Chimie-Biologie, Université du Québec à Trois-Rivières, Trois-Rivières, Québec G9A 5H7 Enol ether attack on cationic ketenes ; formation of functionalized aldehydesand hemiketals: We investigated the possibility of producing hemiketals5 from alkoxyhomoallylicynol ethers 2. Alcohols 1a and 1b were first prepared. Ynolethers 2were prepared from alcohols 1a and 1b. Ynol ethers 2 were then reacted with a source of non-nucleophilic H+ (“solid acid” resin ) in the hope of producing a hemiketal (such as 5). Only hydrolysis products 6and 7 were isolated, no cyclization product could be observed. Using other “non-aqueous” acids (PhCOOH, TsOH, …) and HgO, Hg(OAc)2 or Ru(p-cymene)Cl2as catalysts led to the same undesired hydrolysis products. October2010 ACS PRF# 46293-B1

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