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[α‐(Phenylsulfinyl)‐α‐methylbenzyllithium‐tetramethylethylenediamine] 2 : Crystal Structure of an α‐Sulfinyl “Carbanion”
Author(s) -
Marsch Michael,
Massa Werner,
Baum Gerhard,
Boche Gernot,
Harms Klaus
Publication year - 1986
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.198610111
Subject(s) - carbanion , electrophile , chemistry , benzaldehyde , sulfoxide , dimer , tetramethylethylenediamine , atom (system on chip) , crystal structure , salt (chemistry) , crystallography , medicinal chemistry , organic chemistry , catalysis , computer science , embedded system
The first X‐ray structure analysis of a lithiated sulfoxide showed that the benzylic C‐atom in [PhC̈(Me)S̈(O) Ph]Li is not planar and that there is no interaction between this C‐atom and the Li atom. In the crystalline state, the salt is present as a dimer with a central Li 2 O 2 unit. A new model (right) can be formulated for the diastereofacial differentiation in the reaction of α‐sulfinyl “carbanions” with electrophiles such as benzaldehyde.