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A Fairly Stable Crystalline Silanone
Author(s) -
AlvaradoBeltran Isabel,
RosasSánchez Alfredo,
Baceiredo Antoine,
SaffonMerceron Nathalie,
Branchadell Vicenç,
Kato Tsuyoshi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705644
Subject(s) - ylide , phosphonium , steric effects , substituent , chemistry , crystallography , medicinal chemistry , stereochemistry , polymer chemistry
Silanones 2 substituted by bulky amino‐ and phosphonium ylide substituents have been synthesized and isolated in crystalline form. Thanks to the steric protection and the strong electron‐donating ability of the substituents, silanones 2 are persistent and only slowly dimerizes at room temperature ( t 1/2 =0.5 or 5 h). Structural and theoretical analysis of 2 indicate a short Si=O bond (1.533 Å) and an enhanced polarization toward the O atom compared to Me 2 Si=O owing to the strong π‐electron donation from the phosphonium ylide substituent.