Roy De Selms

ACS 60 Years Emeritus Member – Roy C. De Selms, Ph.D.
September 2017

85 Years of Science and Circumstance

For whatever reason I can’t remember at age 85, I decided to become a chemist when I was 8 years old. My father was overseas during and before WWII, but somehow managed to send me a Chemcraft chemistry set soon thereafter my Grandfather gave me a Bausch & Lomb microscope kit. By age ten I was able to earn enough money working on my Grandmother’s pear orchard in Sacramento at 10 cents/hr. to buy the $25.00 (largest) Chemcraft chemistry set.

My Great Grandparents on my mother’s side came from Germany around Cape Horn to San Francisco in the 1850’s and later settled in and helped found the City of Berkeley. Growing up in Berkeley was a big advantage because the primary and secondary education was unsurpassed and in my spare time I would go up to the University and see the rocks and minerals exhibits at the Hearst Mining building and Bacon Hall where I later had a laboratory. I would also visit the undergraduate labs and scavenge discarded bottles of chemicals, flasks, glass-stoppered bottles, etc. and hike up to the big “C” and wonder what was going on in the building called the (world’s first) Cyclotron. Later I got to meet Nobel Laureate Prof. Glen Seaborg and work in the Lawrence Radiation Laboratory at U.C. Berkeley.

Burbank Jr. High School in Berkeley only offered Spanish at that time so two years of Spanish it was. Then at Berkeley High School I first was able to take German which I knew I would need for chemistry, but not really why, and I had a head start thru my German Grandmother. The reason was that before WWII about 75% of the world’s scientific literature was published in German and I later had to refer to that early literature almost daily for the next forty years. It’s also interesting to note that Germany before WWII was the place to do post doctoral research as well as get advanced degrees. Of course that’s all changed and the U.S. has been the capitol of the scientific world for the last 50 years or so.

When I was half way through high school, my family moved to Seattle. So I finished high school there and went to the U. of Washington for my B.S. in Chemistry. It’s hard to believe, but the tuition then was $48.00/year and the same in the U. C. schools. Incidentally the U. of Washington is the oldest land grant college in the West founded in1861. At the U.W. I was able to arrange summer jobs with Prof. D. M. Ritter doing metal organic syntheses and glass blowing. Had metal organic chemistry been a little more advanced and had I a little more vision, it would have been a great opportunity for me. Unfortunately social life had interfered with getting grades high enough to go directly to one of the better graduate schools.

Fortunately or unfortunately my eyesight was 20/20 but not absolutely perfect. This kept me from flying Air Force jet fighters over North Korea and/or Viet Nam, but also from going into the Astronaut program and possibly to the moon with my science background. Actually my surname would have kept me out of the latter program because they were selecting only personnel with English sounding names.

So in the Fall of ‘54 I found myself at Dartmouth College in Hanover N.H. for a M.S. and hopefully on my way to Harvard for a Ph. D. The school year at Dartmouth went pretty fast with considerable skiing close by and 3 big weekend parties during the year when the population of Hanover doubled in size from 2,700 by importing young ladies from Welsley, Colgate, Colby, etc., since Dartmouth was an all male school at the time, but did go co-ed in the 70’s. For what it’s worth the author of “Animal House” went to school there. Hanover N.H. is very isolated for students without wheels and Dartmouth gives priority to students by the distance they live from the school. So students coming from California, Europe, and Asia have priority over students from Vermont, Mass., or New York making a very good experience for the students. Dartmouth also had a “Famous Speakers” program attended by the whole campus and allowed me to spend an evening with Nobel Laureate Prof. Harold Urey who discovered how to produce Deuterium Oxide (heavy water) from old batteries and Prof.-Dr. Kurt von Schuschnigg who had been the Chancellor of Austria when Hitler took Austria at the beginning of WWII and was a political prisoner for 7 years at Dachau and Sachsenhausen then came to teach at St. Louis University. In my judgement, it’s far better to go to a small school like Dartmouth for undergraduate work than to a large impersonal school like U.C. Berkeley, but definitely go to a large and good graduate school if possible.

Fortuitous circumstantial reasons (a young lady from Santa Cruz) brought me to Stanford U. in the summer of 1955 where I worked for Prof. Harry S. Mosher. My glass blowing experience allowed me to make the first large scale Gas Chromatographs in the world. I also worked on syntheses of pyridines and separations of optically active amyl alcohol. By mutual agreement I decided to stay and worked for my Ph.D. in chemistry in the field of cancer chemotherapy which led to my first JACS publication with Prof. Mosher. The tuition at Stanford in the late 50’s was $1,350.00/year which was paid by teaching assisting and grants. Somehow a grant was not applied for in my last year, but a 2/5 time chemistry teaching position miraculously became available which I could not afford to pass up. One of the chemistry teachers at Palo Alto High School was going to attend classes at Stanford in order to teach AP chemistry. I had been set up, but it was a great experience and convinced me that teaching is the best way to learn.

Human toxicity of Agent Orange was known by mid-1950’s. While at Stanford in 1955 to 1959, Prof. Harry Mosher walked into my lab one day with a small bottle containing a colorless powder. He asked if I would like to work on making analogs of the most toxic chemical known at the time? I was honored by his confidence in me, but when he showed me the structure, 2,3,7,8-tetrachlorodibenzo-p-dioxin, the chemistry didn’t really appeal to me and I respectfully declined. This turned out to be one of the best decisions in my life, because later I found out that this was “Dioxin” a by-product in the manufacture of and the most toxic component of “Agent Orange”.

In general synthetic drugs like Demerol can be patented, but not natural products like Morphine. One of my lab partners at Stanford was working on making analogs of “Demerol” to see if he could find something with the same or better analgesic power, but without its undesirable side effects. This knowledge has been important to me thru numerous surgeries. From experience, I’ve found that most Anesthesiologists don’t let you know a day in advance what medications they’ll be using and in the case of analgesics, they tend to use synthetics that have been patented and lobbied by pharmaceutical companies and make money. This situation has changed somewhat thru the years, but I will always opt for a natural product like morphine which has been used for a thousand years as an analgesic. According to the literature Demerol is not useful below a 50 mg. dose and can require up to 100 times as much to get the same effect as morphine.

Postdoctoral research with Prof. Henry Rapoport at U.C. Berkeley was my next stop. My project was involved with using radioactive C-14 labeled CO2 to trace the entry of carbon into nicotine in growing tobacco plants. We did find that nicotine is an active metabolite in tobacco plants and not just an end product as previously thought. We also traced the path of carbon into nicotine, but I lost tract subsequently of the project. What’s probably more interesting is how this project started. Another professor at U.C. Berkeley, Nobel Laureate Prof. Melvin Calvin, needed radioactive morphine to study its fate when injected into postdocs and graduate students. It’s not easy to label morphine, so they decided to feed C-14 CO2 to opium poppy plants and voila they had it (and that led to our investigation). The result was that morphine is passed thru the body unchanged 95% within experimental error. One very important lesson is that other drugs including some pharmaceuticals are not necessarily metabolized in order to be effective. So when some say that taking vitamins only produces expensive urine, it could be a meaningless statement.

At the end of my PostDoc in 1963, I interviewed with Polaroid Corp. in Cambridge Mass. Where the Director of Research had his office in what had originally been the laboratory of Samuel F. B. Morse, inventor of the telegraph. On this interview I was photographed with the new Polaroid color film before it became available on the market. However, I decided to stay in the Bay area.

My next career step took me about 10 miles north of Berkeley to the Research Labs of the Ortho Division of Chevron Chemicals at Richmond, CA. Here my project was to try to make new pesticides by making as many new organic chemicals as possible to put into screening programs. This was in the 60’s and we were flying blind as far as target molecules were concerned. However organophosphorus compounds were known be a good area for searching and phosphorus NMR spectroscopy turned out to be very interesting. I did make about a pound of an organophosphorus insecticide that was destined for testing on human “volunteers”. I had a few sleepless nights, but that was my job. One of the highlights of working at Ortho was to be able to interact first hand with our consultant, Prof. Saul Winstein, from UCLA. I also met with Alfred Bader, founder of Aldrich Chemicals about one of my compounds that might make it to commercial use. Another highlight, the significance of which, I didn’t appreciate at the time was having a ride in the first Toyota that entered this country. It was a gift from Toyota to Chevron Research and used by the Research Director for obvious reasons. While at Ortho, I designed and taught a course on Heterocyclic Chemistry at U.C. Berkeley (and later at the U. of Rochester in Rochester, NY).

In 1966 I went back to the Research Labs at Eastman Kodak in Rochester NY where I had been from 1959 to 1962. Kodak was a very large (75,000 in Rochester 125,000 world wide and one of the 30 Dow Industrials for many years since its beginning. Kodak was a very paternalistic company where I was able to do a considerable amount of research that was of interest to me as well as beneficial to the company. Some things that came directly or indirectly from my work were Kodak’s version of Xerography, commercial method of making “Super Glue” (cyanoacrylic acid esters), and image modifiers with self-destruct development inhibitors still used in Kodak’s Color Print and Movie Films – none for which I receive any royalties. Most of my 45 publications and patents were done at Kodak and included carbene chemistry, heterocyclics, small rings and rearrangements (including demonstration of steric hindrance to ionization), the first cyano ketene (including stereochemistry of ketene cycloadditions), the first methylene cyclobutenone, work leading to the first cyclobutadiene, and photochemistry (and photographic chemistry).

George Eastman stopped in England on his way to do some big game hunting in Africa in the early 20th C. His main purpose was to visit a competitor, Wratten & Wainwright, Ltd., and try to hire away a bright young chemist named C. E. K. Mees. However Mees was like all employees at that time very loyal and refused the offer. Eastman went on his way and hunted in Africa, but on the way back he stopped to talk to Mees again. This time he asked Mees how soon he could come to Rochester NY, but Mees again said he couldn’t leave his employers. Eastman slyly pointed out that he had just purchased Wratten & Wainwright and that Mees now worked for him. Mees started the Research Labs for Eastman Kodak in RochesterNY.

At the beginning of WWI a situation arose that the dye for allied soldiers’ uniforms was not available outside of Germany. So Kodak offered its services and started making any required dyes. This effort was so successful that Kodak continued making fine chemicals after the war and did this for many years on a non-profit basis to supply the academic community. By the 1950’s that business was done for profit and then eventually superseded, I think, by Aldrich Chemicals.

Of course Eastman Kodak has been the world leader in photography for most of its lifetime, having gained it’s early advantage thru using a flexible cellulose nitrate support that could be rolled up instead of solid glass plates. Several wars have required Kodak’s photographic resources and the first trips into space and to the moon used them. In the beginning of color photography, the process was very time sensitive and the inventors used classical music in the darkroom for precise timing. Even though digital photography was invented at Kodak, it has way outpaced conventional photography by way of convenience and is superseding it except for some very special applications.

Throughout my 27 years at Kodak I was able to meet many outstanding world chemists and even Noble Laureates through the outstanding speakers programs and because of the yearly travel allowance to attend Gordon Research Conferences and other professional meetings. In 1974 I was invited to give a lecture at the Gordon Conference Physical Organic Chemistry section and was quite intimidated when Prof. John D. Roberts from Cal Tech and Prof. Don Cram from UCLA showed up in the first row. I also was fortunate to have supervised doctoral students from the Universities of Heidelberg (Germany) and Geneva (Switzerland) both of which led to JACS and JOC publications.

Something I have always tried to do in this life is what I was happy doing and that was research in organic chemistry. If you can do what makes you happy, then that’s what you will be good at and vice versa. Money is nice, but happiness is essential. Circumstances don’t always come one’s way, but you must learn to roll with the punches and serendipity sure helps.