Syntheses and Reactions of Selenocarboxylic Acids

Abstract

4-Biphenylselenocarboxylic acid [6], selenium isologue of 4-biphenylcarboxylic acid, was synthesized by the reaction of hydrogen chloride in ether with sodium 4-biphenylselenocarboxylate [4']prepared from bis(4-biphenylcarbonyl) diselenide [3] and sodium methoxide. The spectral data of [6], a red solid of mp 39.0∼40.0°C, were specified. [6] changed to [3] by heating, and to bis(4-biphenylcarbonyl) selenide [7] and [3] by heating in hexane. [6]reacted with methanol to give methyl 4-biphenylcarboxylate, [7], and C3 J. Th[6e] reaction of [6] with phenylisocyanate to gave phenylcarbamoyl 4-biphenylselenocarboxylate[13]and with aniline gave 4-biphenylcarboxanilide [14]. [13]changed to [14] by heating.1Adamantaneselenocarboxylic acid (yellow solid of mp 28.0-∼29.0°C) was also synthesized by the same manner as the preparation of [6] and its spectral data were specified.