International Research Experience for Undergraduates

Emilie Gautriaud

2002 Participant


Study of Rearrangement of 1,1 Difluoro-2 Deuterated Methylene Cyclopropane

For the past several years, Dr. Dolbier's research group has been working on gem-difluorocyclopropanes, including their thermal rearrangement. My project consists of studying the thermolysis of 1,1-difluoro-2-deuteratedmethylenecyclopropane to obtain 1,1-difluoro-2,2- dideutero-3-methylenecyclopropane.

Gautriaud Diagram 1

The presence of deuterium in this molecule should allow us to better understand the mechanism of its thermal rearrangement. A large part of my project consists in synthesizing this product.

Gautriaud Diagram 2

I use a novel and highly efficient method reported by Dr Dolbier's group to get a difluorocarbene intermediate, able to perform a difluorocyclopropanation of n-butylacrylate and then to obtain the corresponding gem-difluorocyclopropane. The difluorocarbene precursor used is trimethylsilyl fluorosulfonyldifluoroacetate (TFDA).