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The Hydroboration-Iodination of Dialkylselenoacetylenes to Vinylic Diselenides
31 December 2000 (online)
The hydroboration of dialkylselenoacetylenes 1, generated from alkylseleno bromides and sodium acetylide in liquid ammonia, with dicycloalkylboranes followed by iodination under basic condition produced (Z)/(E)-vinylic diselenides (2/3). The reaction proceeds with a transfer of one cycloalkyl group and smoothly to give major 2 and minor 3 in almost quantitative ratio (2:3=93:7 to 97:3). The hydroboration-iodination process provides a general method for synthesis of (Z)-vinylic diselenides containing cyclic systems.
hydroboration - iodination - diselenoethyne - vinyl - diselenide