Preparation of Fluorinated Phthaloylphosphines and Primary Phosphines as
Precursors for New Fluorinated Anions
Chemistry, Dr. O'Brien
About My Research:
Our research involves finding a simplified method to form primary phosphines and ionic liquids. Preparation of phthaloylphosphide and its ring-substituted derivatives is carried out with ease, and with greatly improved safety. The usage of phosphine and other air-sensitive compounds is the minimal risk of this particular method of preparation. The primary phosphines are hard to prepare, but the pathway proposed by Dr. Brian O’Brien is simple and straightforward. The phthaloylphosphine ion is used to carry out the formation of the primary fluorinated phosphines, by simple organic Sn1 and Sn2 reactions. The primary phosphine derivatives can be converted into ionic liquids again by simple reactions. Production of these fluorine/phosphorus compounds is interesting to industry of fluorinated compounds.
In the student's own words :
"Research is a practical usage of the knowledge that I have gained over the past few years. Being at a small private liberal arts school means that research opportunities are much more notable to those students who take the initiative. I have enjoyed every aspect of my research experience and hope to continue making great memories and progress"
A straightforward method for the preparation an array of fluorinated aryl halides and fluorinated organic derivatives by P-arylation and P-alkylation of phthaloylphosphide ion is described and the method of using the resulting (P-aryl) phthaloylphosphines for preparation of primary arylphosphines and fluorinated organic derivatives of hexafluorophosphate. This is done by a process of combining the primary phosphines with Selectfluor® converting them to tetrafluorophosphoranes, arylpentafluorophosphate anions, and arylphosphonic acid derivatives. This plan is outlined in the scheme below for the aryl derivatives: (Phth = phthaloylphosphino group)
More from this student :
"Research has opened me to so many opinions as an ASC Chemistry major. I have gotten to know my professors in acompletely different setting than the lecture hall. I have met their families, sat and talked about life, and just joked around."
- Jason presented his results at the 2008 Chemistry-Biology Research Symposium