Barton-Kellogg reaction

The Barton-Kellogg reaction is a coupling reaction between a diazo compound and a thioketone to give an episulfide. Desulfurization of the episulfide to alkene can be accomplished by phosphine or by copper powder. This reaction has been pioneered by Hermann Staudinger and therefore the reaction also goes by the name Staudinger-type diazo-thioketone coupling. [Pg.185]

The main advantage of this reaction over the McMurry reaction (see section on McMurry alkenation ) 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. [Pg.187]

Barton-Kellogg Reaction (Barton Olefin Synthesis)... [Pg.66]

Tetrahydrothiopyran-4-one undergoes a Barton-Kellogg reaction with hydrazine hydrate to give the azine 370. Sequential thiadiazolidine formation, oxidation to the thiadiazoline and extrusion of N2 produces the 4,4 -bis(tetra-hydro-4/7-thiopyranylidene) (Scheme 91) <2000JOC4584>. [Pg.847]

The McMurry Reaction is similar to the Barton-Kellogg reaction. However, the McMurry Reaction is unsuccessful for preparing some of the overcrowded alkenes, such as tetra-f rf-butylethylene. ... [Pg.250]

Other references related to the Barton-Kellogg reaction are cited in the literature. ... [Pg.252]

This reaction is related to the Barton-Kellogg Reaction. [Pg.1862]

Figure 1.10 Scheme of the Barton-Kellogg reaction for modified diazo-thioketone coupling for the synthesis of overcrowded alkenes. (Reproduced with permission from Ref [59].)... [Pg.9]

Barton-Kellogg Reaction Barton-McCombie Reaction Barton-Zard Reaction Baudisch Reaction Bauer (see Haller-Bauer Reaction)... [Pg.2]

As discussed in this chapter, various methodologies for C=C bond formation have been developed based on the reaction of W-tosylhydrazones. Traditional base promoted reactions such as the Bamford-Stevens reaction, the Shapiro reaction, the Barton-Kellogg reaction, and Julia-type condensation-fragmentation have already been widely applied for organic synthesis in the past few decades. The palladium catalyzed reaction of A-tosylhydrazones through metal carbene intermediates has attracted increasing attention in recent years. A-Tosylhydrazones are readily available substrates and are stable. They have been proven to be reliable... [Pg.266]

Wang Z. Barton-Kellogg Olefination. Comprehensive organic name reactions and reagents. Wiley... [Pg.372]

Known as Barton-Kellogg olefination, C=C bond formation by the reaction of a thioketone and a ketone through a diazo intermediate has been pioneered by Staudinger s group and further developed by the groups of Barton and Kellogg [22-24]. The thioketone required for the reaction is commonly derived from a... [Pg.241]

The reductive desulfurization of thiiranes has been accomplished with Raney nickel, Li in EtNHa, Zn in HOAc, BusSnH, and P2I4 in DMF but the reaction has seldom been applied to organic synthesis. A noteworthy procedure for preparing moderately hindered tetrasubstituted alkenes, which proceeds via a thiirane intermediate, was developed independently by Barton and Kellogg. The procedure, illustrated in Scheme 14 for the preparation of (34), involved reaction of thiocamphor (30) with diazoalkane... [Pg.980]

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