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Barton‐Kellogg Olefination

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Abstract Coupling of two ketones into alkenes, particularly applicable to the synthesis of moderately to highly hindered alkenes, is generally referred as Barton‐Kellogg olefination. In this reaction, the steric constraints are gradually introduced via sequential processes involving a 1,3‐Dipolar Cycloaddition to form five‐membered Δ 3 ‐1,3,4‐thiadiazoline, followed by the nitrogen elimination to three‐membered episulfide, and finally the sulfur extrusion to afford the alkenes. Although this reaction can be used for the synthesis of asymmetric alkenes from two different ketones, symmetric alkenes will always be formed as by‐products.
Title: Barton‐Kellogg Olefination
Description:
Abstract Coupling of two ketones into alkenes, particularly applicable to the synthesis of moderately to highly hindered alkenes, is generally referred as Barton‐Kellogg olefination.
In this reaction, the steric constraints are gradually introduced via sequential processes involving a 1,3‐Dipolar Cycloaddition to form five‐membered Δ 3 ‐1,3,4‐thiadiazoline, followed by the nitrogen elimination to three‐membered episulfide, and finally the sulfur extrusion to afford the alkenes.
Although this reaction can be used for the synthesis of asymmetric alkenes from two different ketones, symmetric alkenes will always be formed as by‐products.

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