Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents

JN Ngwendson, CM Schultze…

Index: Ngwendson, Julius N.; Schultze, Cassandra M.; Bollinger, Jordan W.; Banerjee, Anamitro Canadian Journal of Chemistry, 2008 , vol. 86, # 7 p. 668 - 675

Full Text: HTML

Citation Number: 7

Abstract

When arylmethyl phosphonium salts are treated with a base (eg, t-BuOK or NaH) they homocouple to form symmetric 1, 2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (eg, ethoxycarbonylmethyltriphenylphosphonium bromide ...