Organic Syntheses : Volume 48 by Peter Yates

By Peter Yates

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Degassed dichloromethane (50 mL) and degassed hexane (100 mL) are added and the mixture is left to settle for 1 h. 7 g (5 1%) Cp(CO),FeCH,SPh as bright yellow crystals, mp 66 "C. 0 mmol) in degassed dichloromethane (75 mL). The resulting dark green mixture is stirred for 5 min, and anhydrous diethyl ether (degassed) is added while stirring. ). The compound slowly abstracts hydride from diethyl ether, and is slightly air- and moisture-sensitive, but can be stored for a few months at 25 "C under nitrogen.

Fischer, who prepared these compounds for the first time in 1964 [61]. Since then these compounds have attracted broad interest, and many hundreds of heteroatom-substituted carbene complexes have been synthesized. Thereby valuable new insights were gained into the nature of the carbon-metal double bond. These complexes are also becoming increasingly important for organic synthesis, both as reagents and as catalysts. 2 the most important synthetic approaches to alkoxy- or (acy1oxy)carbene complexes from non-carbene precursors are sketched.

1 [33]). , sulfur ylides, can cyclopropanate acceptor-substituted olefins by an addition-elimination mechanism. , acceptor-substituted olefins are added to a mixture of a simple alkene and the metathesis catalyst PhWCI,/AlCl,, the metathesis reaction is quenched and small amounts of acceptor-substituted cyclopropanes can be isolated [34]. These observations indicate that there is no sharp borderline between cyclopropanating and metathesis-catalyzing carbene complexes. Fortunately the number of carbene complexes which mediate both cyclopropanation and alkene metathesis is rather small, and in the detailed overview given in the following sections it will become apparent that most carbene complexes are highly selective and thus valuable reagents for organic synthesis.

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