Electric Literature of 499-40-1. Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 499-40-1, Name is (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal. In a document type is Article, introducing its new discovery.
Activation of anisole by organoplatinum(II) complexes: Evidence for rate-determining C-H activation
A study of the basis of selectivity of C-H bond activation of anisole by electrophilic methylplatinum(II) complexes is reported. Anisole reacts with [PtXMe-(NN)] in trifluoroethanol solvent to give methane and [PtXAr(NN)], Ar = 2-, 3-, and 4-anisyl, in 90:8:2 ratio when X = HOB(C6F 5)3 and NN = (2-C5H4N)2CO (DPK) but not when NN = 2,2?-bipyridine. Similar results are obtained when X = triflate or when NN = (2-C5H4N)2NH. Competition between reaction of anisole and anisole-d8 with [PtXMe(NN)], X = HOB(C6F5)3 and NN = DPK, in trifluoroethanol gave an isotope effect kH/kD = 3.6. Several 4-anisyl complexes, [PtClAr(NN)], [PtAr2(NN)], and [PtMeAr(NN)], NN = DPK, DPA, or bipy, were prepared and reacted with HX [X = Cl, OTf, or HOB(C6F5)3]. Reaction of [PtMeAr(NN)], NN = DPK or bipy, with HX gave a detectable hydride [PtXHMeAr(NN)] when X = Cl, followed by loss of methane to give [PtClAr(NN)], but only [Pt(OTf)Ar(NN)] was detected when X = OTf. Reaction with more HOTf gave anisole and [PtX 2(NN)], X = OTf, and no isomerization of the 4-anisyl group to the more favored 2-anisyl group was observed at any stage. The similar reaction of [PtMeAr(NN)] and HOTf in CD3OD/CD2Cl2 gave CHnD4-n (n = 0-4) and mostly 4-MeOC6H 4D. It is argued that the anisole C-H bond cleavage step in anisole activation, or the anisyl-H bond forming step in protonolysis, is responsible for the observed selectivity in these reactions.
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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics