Comparative theoretical study of 1,3-dipolar cycloadditions of allyl-anion type dipoles to free and Pt-bound nitriles.
作者： Maxim L. Kuznetsov , Vadim Yu. Kukushkin , Armando J. L. Pombeiro
DOI: 10.1021/JO902415D
关键词:
摘要: 1,3-Dipolar cycloadditions of a series 12 allyl-anion type 1,3-dipoles X═Y+−Z− (X, Z = CH2, NH, O; Y N(Me), O) to acetonitrile MeC≡N, both free and coordinated PtII PtIV in the complexes trans-[PtCln(NCMe)2] (n 2, 4), were investigated by theoretical methods. The reactivity increases along following sequence dipoles, first three being inert toward nitriles: ON(Me)O < NHN(Me)O NHN(Me)NH CH2N(Me)O OOO ≈ NHONH CH2N(Me)NH NHOO CH2N(Me)CH2 CH2OCH2 CH2ONH CH2OO. thermodynamic stability cycloaddition products (reaction energies) inversely correlates with activation energies exception dioxadiazoles N═C(Me)OONH which cannot exist uncoordinated state. A complete ortho selectivity these reactions is predicted. Coordination MeCN platinum accelerates CH2N(Me)CH2, CH2ONH, particularly stabilizes corresponding products. CH2OCH2, CH2OO, NHONH...
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