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Synthesis and Characterization of Allylic and Propargylic Selenols

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journal contribution
posted on 08.12.2001, 00:00 by El Hassan Riague, Jean-Claude Guillemin
Allylic selenols (2-propene, 2-butene-, 3-methyl-2-butene-, and 2-methyl-2-propeneselenol) are formed by slow addition of n-Bu3SnH to the corresponding diallylic diselenide diluted with tetraglyme or by a two-step reaction sequence involving the addition of the corresponding selenocyanate to LAH and subsequent treatment with an acid. The 2-propyne-, 3-butene-, and 3-butyneselenols have also been synthesized. β,γ-Unsaturated selenols are very unstable compounds at room temperature in the absence of a radical inhibitor. Characterization was performed by 1H, 13C, and 77Se NMR spectroscopy and mass spectrometry.