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A Tin Analogue of Carbenoid: Isolation and Reactivity of a Lithium Bis(imidazolin‐2‐imino)stannylenoid
Author(s) -
Ochiai Tatsumi,
Franz Daniel,
Wu XiaoNan,
Irran Elisabeth,
Inoue Shigeyoshi
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602178
Subject(s) - chemistry , lithium (medication) , reactivity (psychology) , stannate , medicinal chemistry , carbenoid , tin , dimer , oxidative addition , stereochemistry , organic chemistry , catalysis , zinc , rhodium , medicine , alternative medicine , pathology , endocrinology
The lithium bis(imino)stannylenoid (NIPr) 2 Sn(Li)Cl ( 1 ; NIPr=bis(2,6‐di iso propylphenyl)imidazolin‐2‐imino) was prepared by the reaction of LiNIPr with 0.5 equiv of SnCl 2 ⋅diox (diox=1,4‐dioxane) and the ambiphilic character of the compound was demonstrated by investigations into its reactivity. Treatment of 1 with I 2 or MeI yielded the oxidative addition products (NIPr) 2 SnI 2 and (NIPr) 2 Sn(Me)I, respectively. In contrast, the reaction of 1 with one equivalent of Me 3 SiCl resulted in the formation of Me 3 SiNIPr and the chlorostannylene dimer [NIPrSnCl] 2 . Moreover, the substitution reaction of compound 1 with MeLi led to the formation of the methyl‐substituted stannate (NIPr) 2 Sn(Li)Me.