ORGN 369 |
| Siletanes (silacyclobutanes) are an emerging class of silane reagents that attract attention by virtue of their “strain-release Lewis acidity.” We therefore became interested in the synthesis and properties of siletane-derived nucleophiles. Such compounds were expected to display ambiphilic character and reactivity not seen in other systems. For example compounds 1 and 2 can be considered as pseudo-ylides. The method for the multigram preparation of 1 was developed. When investigating reactivity of 1 towards n-BuLi we found that transmetallation of the stannyl moiety competes efficiently with polymerization of siletane ring. Thus, we gained access to 2, which was quenched with different electrophiles. The reaction of 2 with benzophenone, for example, leads to the formation of the corresponding olefin in a one-step process.
|
|
Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |
