Alkenylcarbyne Complexes Derived from the Reactions of OsXCl-(PPh3)3(X=H,Cl) with Propargyl Chloride and Phosphine Ligand-Controlled Transformation of Hydride-Carbyne to Carbene

doi:10.6023/cjoc201608013

Abstract

Reactions of the simple osmium precursors OsHCl(PPh₃)₃(1) or OsCl₂(PPh₃)₃(2) with 3-chloro-3-methylbut-1-yne afforded OsHCl₂(≡CCH=CMe₂)(PPh₃)2(3) or OsCl₃(≡CCH=CMe₂)(PPh₃)2(4),respectively.Treatment of 3 with Ph₂PC≡CPh led to the formation of the tris-diphenyl(phenylethynyl) phosphine alkenylcarbene complex OsCl₂(=CHCH=CMe₂)(Ph₂PC≡CPh)₃(5),while complex 4 underwent simple phosphine ligand substitution with Ph₂PC≡CPh to give OsCl₃(≡CCH=CMe₂)(Ph₂PC≡CPh)₂(6).Presumably,upon the phosphine ligand substitution of PPh₃ in 3 by Ph₂PC≡CPh,the relatively electron-poor nature of the later decreased the electron density of the osmium center,and thus promoted the transformation of the hydride-carbyne to carbene via the 1,2-shift of the hydride ligand from Os to the carbyne carbon,which was then further facilitated by the coordination of a third less bulky Ph₂PC≡CPh ligand to the osmium center to give the stable 18e product 5.

Key words: osmium, carbyne, carbene, diphenyl(phenylethynyl) phosphine, propargyl chloride

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Yang Yu, Cai Tao, Wen Tingbin. Alkenylcarbyne Complexes Derived from the Reactions of OsXCl-(PPh₃)₃(X=H,Cl) with Propargyl Chloride and Phosphine Ligand-Controlled Transformation of Hydride-Carbyne to Carbene[J]. Chin. J. Org. Chem., 2017, 37(1): 176-184.

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OsXCl(PPh₃)₃(X=H,Cl)与炔丙基氯反应合成烯基卡拜配合物及膦配体调控的锇-氢卡拜向卡宾配合物的转化

Alkenylcarbyne Complexes Derived from the Reactions of OsXCl-(PPh₃)₃(X=H,Cl) with Propargyl Chloride and Phosphine Ligand-Controlled Transformation of Hydride-Carbyne to Carbene

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OsXCl(PPh3)3(X=H,Cl)与炔丙基氯反应合成烯基卡拜配合物及膦配体调控的锇-氢卡拜向卡宾配合物的转化