Abstracts of Symposium on Physical Organic Chemistry
53rd Symposium on Organic Reactions
Session ID : P-70
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Novel Transformation of Olefins with a Ruthenium(III) Catalyst
*Yukiko YokogawaMitsuteru HigashimuraKeita ImamuraTsutomu Sakakibara
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Abstract
In recent years various catalytic reactions are caused by the use of ruthenium, such as Grubbs catalyst. Although most of catalysts are useful materials for organic synthesis, they need expensive reagents and many reaction steps to prepare. Then we have investigated novel ruthenium-catalyzed reactions that employed Ruthenium trichloride n-hydrate as a catalyst, because it is commercially available and inexpensive. As a result we found a novel catalytic reaction to obtain two kinds of olefin dimmer in good yield. α-Methystyrene, for example, reacted with RuCl3 n-hydrate to give indene or Markovnikov type, depending on whether THF or benzene is used as the solvent. We also have examined reactions of olefins with alcohols and thiols in a similar manner, and we found alkoxylation and sulfidation of olefins, respectively. In these cases we obtained two kinds of products, Markovnikov type or anti-Markovnikov type, depending on the olefin used as the starting material. The yields were good to moderate and the conversions were high, though dimmers were sometimes included. Compared with alcohols, thiols were highly reactive for olefins. Thus alcohols did not react with acrylamide, but thiols did. As mentioned above, we have developed novel Ru-catalysed reactions and now the reactions of olefins with optically active substances are in progress.
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© 2003 by Symposium on Fundamental Organic Chemistry
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