A convenient synthesis of 9, 9-dialkyl-9, 10-dihydroanthracenes and 10, 10-dialkylanthrones: silicon-mediated regioselective dialkylation of 9, 10-dihydroanthracene

RK Dhar, DK Clawson, FR Fronczek…

Index: Dhar, Raj K.; Clawson, D. K.; Fronczek, Frank R.; Rabideau, Peter W. Journal of Organic Chemistry, 1992 , vol. 57, # 10 p. 2917 - 2921

Full Text: HTML

Citation Number: 14

Abstract

Described is a short and convenient approach to the synthesis of 9, 9-dialkyl-9, 10- dihydroanthracenes, 9, 9, 10-trialkyl-9, 10-dihydroanthracenes, and 10, lO-dialkylanthrones, some of which are otherwise unknown or inaccessible by conventional methods. Deprotonation of 9-(trimethylsilyl)-g, lO-dihydroanthracene (2; 9-(trimethylsilyl)-g, l@ DHA) followed by reaction with alkyl halides (RX) produces Salkyl-S (trimethylsilyl)-9, 1@ DHAa ...