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X‐Ray Structure Investigation of 2,2‐Diphenyl‐1‐(phenylsulfonyl)cyclopropyllithium–Dimethoxyethane (2/3): A Sulfonyl “Carbanion” Having an α‐C Atom with a Tetrahedral Configuration
Author(s) -
Hollstein Werner,
Harms Klaus,
Marsch Michael,
Boche Gernot
Publication year - 1988
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.198808461
Subject(s) - carbanion , sulfonyl , chemistry , delocalized electron , atom (system on chip) , sulfone , dimethoxyethane , tetrahedron , crystallography , computational chemistry , stereochemistry , polymer chemistry , organic chemistry , alkyl , computer science , embedded system , electrode , electrolyte
The stabilization of a neighboring negative charge by a sulfonyl group is also possible when the α‐C atom‐‐‐as in 1 ‐‐‐is not planar but rather tetrahedral in configuration. This finding indicates that a delocalization (p π ‐d π interaction) as in ester enolates and nitronates does not play a significant role in the stabilization of such sulfonyl “carbanions.” Much more important is an n‐σ * interaction, as has also been shown from quantum‐mechanical calculations.