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Studies on the Regio- and Stereoselectivity of Halohydroxylation of 1,2-Allenyl Sulfides or Selenides.
- Source :
-
Journal of Organic Chemistry . 8/20/2004, Vol. 69 Issue 17, p5720-5724. 5p. 6 Charts. - Publication Year :
- 2004
-
Abstract
- It was observed that the halohydroxylation of 1,2-allenyl sulfides or selenides with Br2 (CuBr2 or NBS) or I2 and water demonstrated a fairly good regioselectivity (i.e., the C=C bond that is remote from the S or Se atom was halohydroxylated with the halogen atom connecting to the middle carbon atom and the hydroxyl group connecting to the non-S terminal carbon or Se-substituted terminal carbon atom of the allene moiety), leading to the synthesis of synthetically important 3-organosulfur or seleno-2-haloallylic alcohols. The stereoselectivity depends on the nature of X+ and S or Se, showing a Z-selectivity with the matched Lewis acid-base pair. [ABSTRACT FROM AUTHOR]
- Subjects :
- *HYDROXYLATION
*SELENIDES
*HALOGENS
*CARBON
*ALLENE
*HYDROXYL group
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 69
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 14379976
- Full Text :
- https://doi.org/10.1021/jo049593c