The Barton–Kellogg reaction is a coupling reaction between a diazo compound and a thioketone, giving an alkene by way of an episulfide intermediate.[1][2][3] The Barton–Kellogg reaction is also known as Barton–Kellogg olefination[4] and Barton olefin synthesis.[5]
The Barton-Kellogg reaction
This reaction was pioneered by Hermann Staudinger,[6] and also goes by the name Staudinger type diazo-thioketone coupling.
The main advantage of this reaction over the McMurry reaction is the notion that the reaction can take place with two different ketones. In this regard the diazo-thioketone coupling is a cross-coupling rather than a homocoupling.
^ R. M. Kellogg (1976). "The molecules R2CXCR2 including azomethine, carbonyl and thiocarbonyl ylides. Their syntheses, properties and reactions". Tetrahedron. 32 (18): 2165–2184. doi:10.1016/0040-4020(76)85131-9.