Journal of Organometallic Chemistry p. 145 - 164 (1988)
Update date:2022-07-30
Topics:
Wiberg, Nils
Schurz, Klaus
Silaneimine Me2Si=NSitBu3 (1), which is unstable under normal conditions with regard to dimerization, forms metastable adducts D.Me2Si=NSitBu3 (1.D = 3 with D = Et2O, THF, NEt3, NMe2Et), which can be decomposed thermally to give 1 and D and, can thus serve as sources of 1.Adducts 1.D result from Me2SiXNLi(SitBu3) (X = halogen, amides formed by reaction of Me2SiXNH(SitBu3) with RLi) under LiX elimination in the presence of D and CF3SO3SiMe3.Lewis basicity of D, relative to 1, increases in the order Et2O < THF < NEt3, Cl- < NMe2Et < F-.Similarly resistance of 1.D to decompose into the dimer of 1 and D also increases.Adducts 1.D also decompose by action of excess donor, (viz. 1.OEt2 decomposes in Et2O into ethylene and Me2SiOEt-NHSitBu3, 1.NMe2Et decomposes in NMe2Et under Stevens migration into EtMeNCH2SiMe2NHSitBu3).Reaction of adducts 1.D with water, alcohols and amines, or with organic enes (propene, isobutene, dimethylbutadiene, cyclopentadiene), or with silyl azides (MentBu3-nSiN3), or with benzophenone, respectively, gives the OH and NH bond insertion products, or ene reaction products, or <2 +3> cycloadducts, or a <2 +2> cycloadduct of 1, respectively.
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