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Corey-Winter olefin synthesis
The Corey-Winter olefin synthesis is a series of chemical reactions for converting 1,2-diols into olefins. It is named for the American chemist and Nobelist Elias James Corey and the American-Estonian chemist Roland Arthur Edwin Winter.
Additional recommended knowledge
Often, thiocarbonyldiimidazole is used instead of thiophosgene as shown above.
The reaction mechanism involves the formation of a cyclic thio-carbonate from the diol and thiophosgene. The second step involves treatment with trimethyl phosphite, which attacks the sulphur atom, producing S=P(OMe)3 (driven by the formation of a strong P=S double bond) and leaving a carbene. This carbene collapses with loss of carbon dioxide to give the olefin.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Corey-Winter_olefin_synthesis". A list of authors is available in Wikipedia.|