ORGN 500 |
| As with other electrophile induced desilylation reactions, electrophilic fluorodesilylation takes advantage of the beta effect of silicon and could thus be applied to compounds that have adjacent π systems. This chemistry has been applied to aryl-, vinyl-, allenylmethyl- and allylsilanes for the preparation of various fluorinated compounds. As an attempt to develop novel methodologies toward the preparation of fluorinated heterocycles from readily available organosilanes, we have now prepared allylsilanes featuring a nucleophilic substituent that will intercept the carbocationic intermediate upon addition of an electrophilic source of fluorine. The products resulting from this novel fluorocyclization process are various fluorinated oxygen-containing heterocycles possessing a silyl substituent, which can be used for further functional manipulation. We will describe which parameters favour the fluorocyclization process over the previously described fluorodesilylation. These parameters include the electrophilic source of fluorine, the nucleophile, the substituents on the silicon and the reaction conditions.
|
|
New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Ballroom B, Oral
Division of Organic Chemistry |
