Thiophene formation

Thionation of a ketone

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Sn2

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The activated thionating ylid forms a sulfur-carbon bond with the ketone, while the ketone forms an oxygen-phosphorus bond. A strained 4-membered intermediate is formed which then breaks down to form the thioketone (thione) product. This can occur twice in the same molecule, leading to a dithioketone.

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