Synthesis of (Z)-thiobutenynes using NaOH or TBAOH as activator: a comparative study

Synthesis of (Z)-thiobutenynes using NaOH or TBAOH as activator: a comparative study

Santana, Amanda S.; Viana, Luiz H.; Hurtado, Gabriela R.; Cassemiro, Nadla S.; Carvalho, Diego B. de; Jr, Palimécio G. Guerrero; Baroni, Adriano C. M.

Abstract:

Organylthioenynes have became useful synthons recently, due their possible applications on the synthesis of enediynes and thiophenes. Recently the preparation of (Z)-thiobutenynes through hydrothiolation of 1,3-diacetylenes using NaBH4 and C4H9SSC4H9 to generate nucleophilic sulfur species such as BuS- and PhS- was reported by us. This systematic study allowed us to understand the limitations and potential of this methodology in the preparation of (Z)-thiobutenynes. However, (Z)- thiobutenyne 2, was obtained in low yield (40%) using this methodology.

Organylthioenynes have became useful synthons recently, due their possible applications on the synthesis of enediynes and thiophenes. Recently the preparation of (Z)-thiobutenynes through hydrothiolation of 1,3-diacetylenes using NaBH4 and C4H9SSC4H9 to generate nucleophilic sulfur species such as BuS- and PhS- was reported by us. This systematic study allowed us to understand the limitations and potential of this methodology in the preparation of (Z)-thiobutenynes. However, (Z)- thiobutenyne 2, was obtained in low yield (40%) using this methodology.

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DOI: 10.5151/chempro-14bmos-R0382-1

Referências bibliográficas

• [1] 1 Dabdoub, M. J.; Dabdoub, V. B.; Lenardão, E. J.; Hurtado, G. R.; Barbosa, S. L.; Guerrero Jr. P. G.; Nazário, C. E. D.; Viana, L. H.; Santana, A. S.; Baroni, A. C. M. Synlett 2009, 986.
• [2] 2 Freeman F.; Lu H.; Zeng, Q. J. Org. Chem. 1994, 59, 4350.

Como citar:

Santana, Amanda S.; Viana, Luiz H.; Hurtado, Gabriela R.; Cassemiro, Nadla S.; Carvalho, Diego B. de; Jr, Palimécio G. Guerrero; Baroni, Adriano C. M.; "Synthesis of (Z)-thiobutenynes using NaOH or TBAOH as activator: a comparative study", p-382-382. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0382-1