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37.2.3.1.3 Variation 3: Ylide Generation by Transylidation of a Phosphonium Ylide

DOI: 10.1055/sos-SD-037-00188

Aggarwal, V. K.; Crimmin, M.; Riches, S.Science of Synthesis, (200837327.

An alternative method for the synthesis of alk-2-enylidenearsoranes is by the transylidation of a phosphonium ylide with an arsonium salt under aprotic conditions. The reaction occurs as a result of the energy gained from forming the P=O bond. Subsequent addition of an aromatic aldehyde to the generated arsonium ylide results in a stereospecific epoxidation yielding trans-epoxides 19 in moderate yields (3563%).[‌38‌] The reaction scope is limited to aromatic aldehydes and only a single alk-2-enylidene partner has been described (Scheme 10).

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