Regiospecific hydroselenation of terminal acetylenes using aluminum phenylselenolate anions

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9005-9008

  Dabdoub, Miguel J ^a   Cassol, Tânia M ^a   Batista, Antonio C F ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; SELENIDE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ISOMER; METHODOLOGY; REACTION ANALYSIS;

EID: 0030577498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02114-4     Document Type: Article

References (16)

1. 1. For a review on the synthesis of vinyl selenides see: Comasseto, J. V. J. Organomet. Chem. 1983, 255, 131.
2. 2. Kuniyasu, H.; Ogawa, A.; Sato, K. I.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525.
3. 3. Gosselk, J.; Wolters, E. Z. Naturforsch 1962, 17b, 131.
4. 4. Gosselk, J. Angew. Chem., Int. Ed. Engl. 1963, 2, 660.
5. 5. Kataev, E. G.; Petrov, V. N. Zh. Obshch. Khim. 1962, 32, 3699.
6. 6. Kataev, L. M.; Anonimova, L. N.; Yuldasheva, L. K.; Kataev, E. G. Zh. Obshch. Khim. 1962, 52, 3965.
7. 7. Comasseto, J. V.; Ferreira, J. T. B.; Petragnani, N. J. Organometal. Chem. 1981, 216, 287.
8. 8. Raucher, S. J. Org. Chem. 1977, 42, 2950.
9. 9. Feiring, A. E. J. Org. Chem. 1980, 45, 1962.
10. 10. Bartlett, P. A.; Chouinard, P. M. J. Org. Chem. 1983, 48, 3854.
11. 11. Similar results has been described for reaction of diphenyl ditelluride with DIBAL-H: asaki, K.; Aso, Y.; Otsubo, T.; Ogura, F. Chem Lett. 1989, 607.
12. 9 was formed at the 70:30 ratio as determined by gas chromatography.
13. 13. Dabdoub, M. J.; Cassol, T. M. Tetrahedron 1995, 51, 12971.
14. 14. Excess of acetylene used can be recovered after work-up by distillation under reduced pressure.
15. 15. Alternatively, triisobutylaluminum can be used in the presence of a free hydroxyl group: Groh, B. E. Tetrahedron Lett. 1991, 52, 7647.
16. 16. For entries 4-7 triethylaluminum (18.0 mmol, 9.0 mL, 2.0 M in toluene) was added to the freshly distilled acetylene containing the free hydroxyl group (18.0 mmol) at 0 °C in a separate round bottomed flask under nitrogen.