SILICON-MODIFIED METAL-AMMONIA REDUCTION OF FLUORENE

The metal—ammonia reduction of aromatic and polynuclear aromatic compounds, known as the Birch reduction when alcohols are employed as proton sources, represents an important method for the synthesis of hydroaromatic compounds.1The regiochemistry of this reduction is dictated primarily by the electron density distribution in the anionic intermediates. We have been exploring methods for regiochemical control in this reaction and have shown that a trimethylsilyl group can be used to alter regiochemistry, and, after its subsequent removal, afford a “misoriented” Birch reduction product.2. © 1990, American Chemical Society. All rights reserved.