Science of Synthesis

Ulfkjær, A.; Pittelkow, M., Science of Synthesis Knowledge Updates, (2018) 1, 200.

1-(Vinylsulfanyl)alk-1-yne ‌149‌ (see ‌Scheme 106‌, Section ‌24.4.3.5.4.1.4‌ for synthesis) has been tested for its ability to act as a multifunctional ligand by reaction with metal carbonyls such as nonacarbonyldiiron(0), octacarbonyldicobalt(0), and bis(acetonitrile)decacarbonyltriosmium to give products ‌150‌ (‌Scheme 109‌).[‌28‌] Reaction with nonacarbonyldi­iron(0) reveals that ‌149‌ acts as a multifunctional ligand through six-electron donation by a sulfur atom (two electrons) and the alkyne group (four electrons). Reaction with octacarbonyldicobalt(0) and bis(acetonitrile)decacarbonyltriosmium only leads to four-electron donation through the alkyne group. All compounds maintain the Z configuration of the alkene throughout the reaction sequence.

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