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Carbonium ion rearrangements controlled by the presence of a silyl group

โœ Scribed by Ian Fleming; Shailesh K Patel

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
232 KB
Volume
22
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Tertiary alcohols with a y-silyl group (3) generally undergo a simple carbonium ion rearrangement in acid giving a single alkene product (4) with loss of the silyl group.

We reported earlier several examples of carbonium ion rearrangements of the general type (1 + 2) in which the migrating group R has been a diphenylphosphinoyl group, 2 a phenylthio

๐Ÿ“œ SIMILAR VOLUMES

Evidence for a carbonium ion rearrangeme
Evidence for a carbonium ion rearrangement in the reaction of triisobutylaluminum and 1,3,3-trimethylcyclopropene
โœ Herman G. Richey Jr.; Barry Kubala; Mark A. Smith ๐Ÿ“‚ Article ๐Ÿ“… 1981 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 212 KB

Formation of acyclic products in the reaction of triisobutylaluminum and 1,3,3trimethylcyclopropene can reasonably be ascribed to a carbonium ion rearrangement. This suggestion supports the mechanism for carbalumination of alkenes proposed by Eisch.

The 2-methylbut-2-enyl(diphenyl)silyl gr
The 2-methylbut-2-enyl(diphenyl)silyl group: A silyl group easily converted to hydroxyl in the presence of a 1,2-disubstituted C๎—ปC double bond
โœ Ian Fleming; Stephen B.D. Winter ๐Ÿ“‚ Article ๐Ÿ“… 1993 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 260 KB

The 2-mcthylbut-2-cnyl(diphcnyl)silyl group can be introduced into a variety of organic strucwrcs by way of the cuprate reagent 4. and h can then be converted into a hydroxyl group, even in Ihc prcscnce or a C=C double bond,