Two step conversion of selenothioacetic acid S-butyl ester to 1,3-oxaselenolanes via regio- and stereoselective ring opening of oxiranes

Chemistry Letters

Volumn , Issue 6, 1997, Pages 545-546

  Murai, Toshiaki ^a   Fujii, Makiko ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031535687     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.545     Document Type: Article

References (31)

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18. 20OSSe: C, 44.94; H, 7.54%. Found; C. 45.13; H, 7.57%.
19. 20OSSe: C, 44.94; H, 7.54%. Found: C, 44.77; H, 7.40%.
20. The similar cyclization of β-hydroxyetliyl vinyl selenide 8 was reported to give 1,3-oxaselenolane 9, but in only 2% yield (eq 2): N. K. Gusarova, B. A. Trofimov, V. A. Potapov, S. V. Amosova, and L. M. Sinegovskaya, Zh. Org. Chem., 20, 484 (1984); S. V. Amosova, V. A. Potapov, N. K. Gusarova, and B. A. Trofimov, Zh. Org. Chem., 25, 2283 (1989). Formula Presented
21. The similar cyclization of β-hydroxyetliyl vinyl selenide 8 was reported to give 1,3-oxaselenolane 9, but in only 2% yield (eq 2): N. K. Gusarova, B. A. Trofimov, V. A. Potapov, S. V. Amosova, and L. M. Sinegovskaya, Zh. Org. Chem., 20, 484 (1984); S. V. Amosova, V. A. Potapov, N. K. Gusarova, and B. A. Trofimov, Zh. Org. Chem., 25, 2283 (1989). Formula Presented
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28. The stereochemisty of 3g was determined by the coupling constant (J = 12.0 Hz) of the protons on the carbons attached to selenium and oxygen atoms.
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30. C. H. Beherens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); J. March, "Advanced Organic Chemistry," John Wiley & Sons, Inc., New York (1992), p 368.
31. 1H NMR spectra.