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Birch reduction of benzenesulfonamide and benzenephosphonic acid

Author

Tony Ping-Fong Niem, University of the Pacific

Date of Award

1965

Document Type

Thesis

Degree Name

Master of Science (M.S.)

Department

Graduate School

First Advisor

Charles Matuszak

First Committee Member

Donald Wedegartner

Second Committee Member

Richard Dodge

Abstract

The use of an alkalai metal dissolved in liquid ammonia and a proton source such as alcohol to affect partial reduction of aromatic compounds, commonly known as the BIrch reduction, has proven to be a synthetic procedure of great utility. (1) The flexibility and usefulness of this reaction has attracted increasing attention in recent times, primarily by BIrch (1,2). The overall reaction occuring during the Birch reduction of benzene is indicated by Figure 1. [see PDF]

Birch has suggested that the reaction may proceed by the transfer of one electron to the aromatic nucleus to give a radical anion or a transfer of two electrons to form a dianion. (2,3,4) Either intermediate would then be a very strong base and would react promptly with proton donors such as alcohols, water, or ammonium salts. Figure 2 [see PDF]

Pages

43

Recommended Citation

Niem, Tony Ping-Fong. (1965). Birch reduction of benzenesulfonamide and benzenephosphonic acid. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/392