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Regioselective and stereoselective cleavages of P–S/C–S bonds by lithium and the formation of P-stereogenic functional phosphine derivatives

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Various menthyl-containing phosphinothioates were prepared. Using these compounds, an unusual phosphorus-promoted cleavage of the C–S bond with lithium-naphthalene was examined. The C–S/P–S cleavages could be controlled by the amount of… Click to show full abstract

Various menthyl-containing phosphinothioates were prepared. Using these compounds, an unusual phosphorus-promoted cleavage of the C–S bond with lithium-naphthalene was examined. The C–S/P–S cleavages could be controlled by the amount of naphthalene and temperature applied. Also, the P–S cleavage was confirmed to retain the configuration about the P and this feature was used for achieving a stereospecific formation of the C–P bond.

Keywords: regioselective stereoselective; lithium formation; stereoselective cleavages; bonds lithium; formation; cleavages bonds

Journal Title: Organic chemistry frontiers
Year Published: 2020

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