Regio- and Stereochemistry of Methoxyselenenylation of Acyclic Allylic Alcohol Derivatives and Allylic Phenylselenides

Bulletin of the Korean Chemical Society

Volumn 18, Issue 8, 1997, Pages 800-802

  Kim, Kwan Soo ^a   Ahn, Kwang Ook ^a   Park II, Jong ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0642365311     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. Nicolaou, K. C.; Petasis, N. A. Selenium in Natural Products Synthesis; CIS, Inc.: Philadelphia, 1984.
2. Liotta, D.; Zima, G.; Saindane, M. J. Org. Chem. 1982, 47, 1258-1267.
3. Cooper, M. A.; Ward, A. D. Tetrahedron Lett. 1995, 36, 2327-2330.
4. Kim, K. S.; Park, H. B.; Kim, J. Y.; Ahn, Y. H.; Jeong, I. H. Tetrahedron Lett. 1996, 37, 1249-1252.
5. Haughan, A. F.; Knight, J. R.; Sweeney, J. B. Tetrahedron Lett. 1994, 35, 1781-1784.
6. Although the yield was not high, the regioisomers were not detected at all in the reaction mixture.
7. Acid catalyzed transacetalization occurred probably by acidic 2,6-di-t-butylpyridinium bromide which was generated during the reaction.
8. Takahashi, T.; Nagashima, H.; Tsuji, J. Tetrahedron Lett. 1978, 799-802.
9. The yield of products 32 and 33 was low because the rate of the methoxyselenenylation became slower than that of the decomposition of phenylselenenyl bromide to diphenyldiselenide at low temperature, but other isomers or products were not produced.
10. Barton, D. H. R.; Hall, M. B.; Lin, Z.; Parekh, S. I.; Reibenspies, J. J. Am. Chem. Soc. 1993, 115, 5056-5059.
11. Burling, F. T.; Goldstein, B. M. J. Am. Chem. Soc. 1992, 114, 2313-2320.
12. 13C NMR spectroscopy. See: Schmid, G. H.; Garratt, D. G. Tetrahedron Lett. 1975, 3991-3994.