Preparation of arylpropiolate esters from trichlorocyclopropenium cation and elaboration of the esters to unsymmetrical 1, 4-pentadiyn-3-ones and unsymmetrical …

DH Wadsworth, SM Geer, MR Detty

Index: Wadsworth, Donald H.; Geer, Susan M.; Detty, Michael R. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 16  p. 3662 - 3668

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Citation Number: 62

Abstract

The addition of aromatic compounds including thiophene, naphthalene derivatives, and some benzene derivatives to trichlorocyclopropenium cation gave nearly quantitative yields of l-aryl-2, 3, 3-trichlorwydopropenes. Alcoholysis of the cyclopropene derivatives gave either arylpropiolate esters or arylpropiolate orthoesters (in the presence of added amine base). The arylpropiolates can be converted to unsymmetrical 1, 4-pentadiyn-3-ones by ...