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To Rearrange or not to Rearrange: Reactivity of NHCs towards Chloro‐ and Hydrostannanes R 2 SnCl 2 ( R = Me, Ph) and Ph 3 SnH
Author(s) -
Schneider Heidi,
Krahfuß Mirjam J.,
Radius Udo
Publication year - 2016
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201600271
Subject(s) - chemistry , reactivity (psychology) , stannane , ring (chemistry) , yield (engineering) , medicinal chemistry , adduct , tin , hydrolysis , organic chemistry , materials science , medicine , alternative medicine , pathology , metallurgy
The reaction of 1,3‐di iso propylimidazolin‐2‐ylidene ( i Pr 2 Im) with diphenyldichlorostannane and dimethyldichlorostannane, respectively, leads to the formation of the adducts ( i Pr 2 Im) · SnPh 2 Cl 2 ( 1 ) and ( i Pr 2 Im) · SnMe 2 Cl 2 ( 2 ). These compounds are stable in solution to temperatures up to 80 °C for several days and rearrangement to backbone‐tethered bis(imidazolium) salts or ring expansion reaction to six membered heterocyclic rings was not observed. The reaction of i Pr 2 Im with triphenylstannane Ph 3 SnH leads to reductive dehydrocoupling of the stannane to yield distannane Sn 2 Ph 6 and i Pr 2 ImH 2 . Thus, the reactivity of these tin compounds is completely different compared to those of the lighter congener silicon, for which rearrangement (chlorides) and NHC ring expansion (hydrides) was reported earlier.