Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base

Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25–80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hyd...

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Bibliographic Details
Published in:Tetrahedron letters 2012-10, Vol.53 (43), p.5733-5738
Main Authors: Santana, Amanda S., Carvalho, Diego B., Casemiro, Nadla S., Hurtado, Gabriela R., Viana, Luiz H., Kassab, Nájla M., Barbosa, Sandro L., Marques, Francisco A., Guerrero, Palimécio G., Baroni, Adriano C.M.
Format: Article
Language:English
Subjects:
(Z)-Organylthioenynes
Anions
Butanethiol (C4H9SH)
Hydroxides
Organylthiolate anions
Sodium
Sodium hydroxide (NaOH)
Synthesis (chemistry)
Tetrabutylammonium hydroxide (TBAOH)
Tetrahedrons
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Summary:Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25–80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hydrothiolation of buta-1,3-diynes was more rapid and efficient, providing (Z)-organylthioenynes in good to excellent yields (70–95%).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.08.003