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 | Zendy

Hollstein Werner | Zendy; Harms Klaus | Zendy; Marsch Michael | Zendy; Boche Gernot | Zendy

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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.

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