DEVELOPMENTS IN THE SYNTHESIS OF ZWITTERIONIC OLEFIN CATALYSTS

By

H. JERROLD MILLER

A DISSERTATION PRESENTED TO THE GRADUATE SCHOOL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULHLLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY

UNIVERSITY OF FLORIDA

1997 ACKNOWLEDGEMENTS

First and foremost, I need to thank my parents. Because of them, I am

who I am today, and without their guidance, support, and love, none of this would have been possible. I haven't been the closest son since I moved away,

first to college and then to grad school, but just knowing that they loved me and were there if I needed them was comforting. I also want to thank my

sister, Kathie, who has been very supportive and a great sister.

My two advisors, Dave Richardson and Jim Boncella, were obviously

instrumental in my conversion from a short order cook, following recip>es of others, into a first class chef, making my own recipes for others to follow.

Dave has shown me the importance of understanding fundamental concepts, and has been extremely successful in finding ways to motivate me in my less productive times. His enthusiasm for my chemistry has been very refreshing and often has helped me push that extra yard to get the results. In the last five years, he has become a good friend, as well as a mentor. Jim has shown me the importance of keeping track of the literature. He has worked hard to break me of my habit of reinventing the wheel. Most importantly, Jim taught me everything I know about working with air- and moisture-sensitive chemicals, without which none of this dissertation would have been successful. He has given me the skills that will allow me to be successful for the rest of my career, for which I am eternally grateful.

11 The author wishes to acknowledge Dr. Khalil Abboud, not only for

solving and helping interpret all of the crystal structures, but also for being

very patient with the author over the last four years.

All members, both past and present, of the Richardson and Boncella

groups also need to be recognized. They include Perla Izsak, Steve Wang,

Ryan Mills, Jon Penney, Carlos Ortiz, Dan Vandelende, Will Vaughn, Larry

Villaneueva, Laura Blosch, Celeste Regino, Ken Weakly, Derika Rivers,

Maureen Burkhart, Tu-cai Zheng, Faisal Shafiq, and George Alameddin. I

especially need to thank Percy Doufou, Joy Mendez, Matt Ryan, and Dave

Knoeppel for being great friends as well as coworkers. Unfortunately, there is not room or time for me to explain how instrumental all of these people have been in my development with their support, advice, criticism, humor,

and friendship, so just let me say THANKS.

Two special friends require special recognition. Tom Hayes has been a best friend for the last eight years, and making the trip from Ohio to Horida was especially easy knowing such a good friend was going with me.

Dominick Valenti became a great friend in the last four years, and many questions about both chemistry and women were solved by the two of us over drinks at the Porpoise and elsewhere.

Of course, I need to acknowledge Sheeba, Harry, and Jenny for their never-ending love and loyalty. I could almost feel my blood-pressure dropping as I got a therapeutic cuddle from any of the three of them.

Finally, and most importantly, I need to thank my new wife. Heather. She has made the last four years of my life wonderful, and I look forward to spending the rest of our lives together. There have been many times when things seemed terrible, and I felt like it would never get better, but her love and support has help>ed me p>ersevere, and I will love her forever.

Ill TABLE OF CONTENTS

ACKNOWLEDGEMENTS ii

ABSTRACT vii CHAPTERS

1 INTRODUCTION 1

History of Heterogeneous Systems 1 History of Homogeneous Systems 4

2 APPLICATION OF