Volume 29, Issue 1
Preparative Organic Chemistry
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ChemInform Abstract: Electron Transfer Processes. Part 64. Homolytic Base-Promoted Aromatic Alkylations by Alkylmercury Halides.

G. A. RUSSELL

G. A. RUSSELL

Dep. Chem., Iowa State Univ., Ames, IA 50011, USA

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P. CHEN

P. CHEN

Dep. Chem., Iowa State Univ., Ames, IA 50011, USA

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B. H. KIM

B. H. KIM

Dep. Chem., Iowa State Univ., Ames, IA 50011, USA

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R. RAJARATNAM

R. RAJARATNAM

Dep. Chem., Iowa State Univ., Ames, IA 50011, USA

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First published: 24 June 2010

Abstract

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ChemInform Abstract

Electron transfer chain reactions leading to substitution in electronegatively substituted benzene derivatives can be observed with alkylmercury halides in the presence of proton acceptors such as DABCO. Such processes occur in the photolysis of tBuHg-halides with benzaldehyde, phenones, phthalimides and other disubstituted benzenes as well as in the homolytic cyclization to α-tetralone. A mechanism involving radical adducts and radical anions is discussed.

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