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Formation of an Imino‐Stabilized Cyclic Tin(II) Cation from an Amino(imino)stannylene
Author(s) -
Ochiai Tatsumi,
Franz Daniel,
Irran Elisabeth,
Inoue Shigeyoshi
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500607
Subject(s) - tin , chemistry , substituent , trimethylsilyl , adduct , medicinal chemistry , reagent , lewis acids and bases , azide , stereochemistry , trimethylsilyl azide , organic chemistry , catalysis
The novel amino(imino)stannylene 1 was prepared by conversion of HNIPr (NIPr=bis(2,6‐diisopropylphenyl)imidazolin‐2‐imino) with one equivalent of Lappert’s tin reagent (Sn[N(SiMe 3 ) 2 ] 2 ). Treatment of 1 with DMAP (4‐dimethylaminopyridine) yields its Lewis acid–base adduct 2 . The reaction of 1 with one equivalent of trimethylsilyl azide results in replacement of the amino group at the tin center by an N 3 substituent with concomitant elimination of N(SiMe 3 ) 3 to afford dimeric [N 3 SnNIPr] 2 ( 3 ). Remarkably, the reaction of 1 with B(C 6 F 5 ) 3 produces the novel tin(II) monocation 4 + [MeB(C 6 F 5 ) 3 ] − comprising a four‐membered stannacycle through methyl‐abstraction from the trimethylsilyl group.