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The Generation of Aryl Anions by Double Electron Transfer to Aryl Iodides from a Neutral Ground‐State Organic Super‐Electron Donor
Author(s) -
Murphy John A.,
Zhou Shengze,
Thomson Douglas W.,
Schoenebeck Franziska,
Mahesh Mohan,
Park Stuart R.,
Tuttle Tell,
Berlouis Leonard E. A.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200700554
Subject(s) - aryl , chemistry , electron , ground state , halide , planar , electron transfer , photochemistry , ketone , atomic physics , organic chemistry , physics , alkyl , computer graphics (images) , quantum mechanics , computer science
It takes two to cyclize : Aryl halides are reduced to aryl anions by double electron transfer from the neutral ground‐state electron donor 1 (see scheme), as shown by the formation of a cyclic ketone ( 2 ). The reduced compound ( 3 ) is also formed. Calculations show that the loss of two electrons from 1 is both thermodynamically and kinetically viable and generates a more planar resonance‐stabilized structure.