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Synlett 1997; 1997(8): 891-892
DOI: 10.1055/s-1997-959
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The Hydroboration-Iodination of Dialkylselenoacetylenes to Vinylic Diselenides

De-Yu Yang* , Xian Huang
  • *Department of Chemistr, Hangzhou University, Hangzhou 310028, China
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Publication Date:
31 December 2000 (online)

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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