The Generation of Aryl Anions by Double Electron Transfer to Aryl Iodides from a Neutral Ground‐State Organic Super‐Electron Donor | Zendy

Murphy John A. | Zendy; Zhou Shengze | Zendy; Thomson Douglas W. | Zendy; Schoenebeck Franziska | Zendy; Mahesh Mohan | Zendy; Park Stuart R. | Zendy; Tuttle Tell | Zendy; Berlouis Leonard E. A. | Zendy

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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.

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