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Addition of a related Grignard reagent to epoxides has been shown to produce pyrans. However, this reagent is prepared in two steps in modest yield. Moreover, the Grignard formation was found to be highly prone to Wurtz coupling in our hands, van der Louw, J.; van der Baan, J. L.; Out, G. J. J.; de Kanter, F. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron 1992, 48, 9901.
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Addition of a related Grignard reagent to epoxides has been shown to produce pyrans. However, this reagent is prepared in two steps in modest yield. Moreover, the Grignard formation was found to be highly prone to Wurtz coupling in our hands, van der Louw, J.; van der Baan, J. L.; Out, G. J. J.; de Kanter, F. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron 1992, 48, 9901.
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This result was obtained by using aged catalyst. The employment of freshly prepared Wilkinson's catalyst resulted in a significantly slower reaction, albeit with better levels of selectivity. For a mechanistic study and lead references see: Evans, D. A, Fu, G. C, Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679
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This result was obtained by using aged catalyst. The employment of freshly prepared Wilkinson's catalyst resulted in a significantly slower reaction, albeit with better levels of selectivity. For a mechanistic study and lead references see: Evans, D. A.; Fu, G. C.; Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679.
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