Addition of ICI to Vinylsilanes
- 1 January 1978
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 8 (5) , 291-299
- https://doi.org/10.1080/00397917808065624
Abstract
In an earlier paper1 from this laboratory describing the stereoselective synthesis of vinyl halides from vinylsilanes, we reported the formation of trans-l-iodo-l-hexene from cis-l-tri-methylsilyl-l-hexene by reaction with an acyl hypoiodite followed by fluoride ion-induced elimination of the elements of trifluoro-acetoxytrimethylsilane: Serious drawbacks to this approach include low yields of adduct formation and use of an expensive silver reagent.Keywords
This publication has 4 references indexed in Scilit:
- Cleavage of the silicon-carbon bond by fluoride ion in triorganosilyloxiranes. The stereochemistry of substitution at oxiranyl carbon.Tetrahedron Letters, 1976
- The stereospecific synthesis of vinyl halides using a vinylsilane as the synthetic precursorTetrahedron Letters, 1974
- Geometric configuration and etherification reactions of some naturally occurring 9-hydroxy-10,12-, and 13-hydroxy-9,11-octadecadienoic acidsThe Journal of Organic Chemistry, 1967
- Vinylsilanes, Chlorovinylsilanes and β-Styryltrimethylsilane. Further Studies on the α-Silicon Effect and β-Eliminations Involving Silicon1Journal of the American Chemical Society, 1954