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X‐Ray Structure Analysis of the Li 2 ‐Compound of Bis(trimethylsilyl)metnyl Phenyl Sulfone; Structural Units of an α‐Sulfonyl‐ and a Complex‐Stabilized ortho ‐Sulfonyl‐“Carbanion”
Author(s) -
Hollstein Werner,
Harms Klaus,
Marsch Michael,
Boche Gernot
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198712871
Subject(s) - carbanion , sulfone , sulfonyl , chemistry , trimethylsilyl , dimer , crystal structure , ether , monomer , stereochemistry , medicinal chemistry , crystallography , polymer chemistry , organic chemistry , polymer , alkyl
The formation of C‐Li‐O‐S‐C five‐membered rings is the most important characteristic in the double lithiation of bis(trimethylsilyl)methyl phenyl sulfone 1 (R R′ H), in which 2 is formed. 2 is present as dimer in the crystal; the two monomers are coupled via Li 2 O 2 four‐membered rings. The structure in the crystal is stabilized by four ether ligands per dimer. There are no interactions between Li ⊕ and the “carbanionic” C(SiMe 3 ) 2 groups. The sp 2 orbital of the ortho C‐atom of 2 points to the midpoint between the two Li ⊕ ions.