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Synthesis

What’s In A Name?

June 21, 2010 | A version of this story appeared in Volume 88, Issue 25

I congratulate Carmen Drahl on her article on named chemical reactions, and especially for choosing a dramatic case: the Mizoroki-Heck reaction (C&EN, May 17, page 31). Both inventors had a cruel personal bend in their respective careers despite glamorous success and acclamation from the chemical community.

Tsutomu Mizoroki succumbed to pancreatic cancer only nine years after his breakthrough discovery of the palladium-catalyzed reaction. Richard F. Heck, despite an excellent publication record in ACS journals, lost funding, doesn’t have a single entry in PubMed, and is relegated to the eternal waiting list for the Nobel Prize. I fully agree with Victor A. Snieckus that Heck’s nomination for the Nobel Prize is overdue, also in remembrance of Mizoroki.

Raffaello Masciadri
Münchenstein, Switzerland

The article about named chemical reactions brought to mind my experience with a named reaction. More than 60 years ago, while trying to radiocarbon-label steroids, I chanced upon a previously unknown reaction. Hoping to retrieve a minuscule amount of product, I tried a method of direct introduction of radiocarbon into the steroid ring system.

Instead, the reaction went by an unusual intermediate directly into the steroid ring in almost quantitative yield and at the highest specific activity then possible. When I submitted this surprising finding in 1949 as a Comunication to the Journal of the American Chemical Society, it was turned down. I was asked to resubmit it as a Note.

That Note, which lay on the desk of the journal editor at Harvard, caught R. B. Woodward’s eye and immediately I was called and asked for all the details. This reaction enabled him to introduce the last carbon into his steroid nucleus and go on to complete the total synthesis of cortisone. He gave me ample credit in his keynote talk and paper for my help. This reaction also made it possible for biochemists to establish cholesterol as the precursor of the steroid hormones in the body and to identify the intermediate steps in the biosynthesis of these hormones. Steroids labeled with C-14 by this method have found good use in biological science.

Perhaps because I was a lone organic chemist in a medical school, the only time I was asked to present my work to any department or established scientific group was at the International Congress of Organic Chemists in Zurich in 1955. I gave the opening paper attended by a front row of European Nobel Laureates. Also, although several footnotes mentioned the “Fujimoto reaction” in journals, it was probably not until a 1969 review article titled “The Fujimoto-Belleau Reaction” by J. Weil-Raynal was published in the journal Synthesis that this name appeared. This also recognized that Belleau had independently arrived at this reaction with a different compound and that his finding was published after my Note. As has been mentioned in your article, how a named reaction is received probably depends on science and politics.

George I. Fujimoto
San Diego

I enjoyed the article on name reactions. I’ve admired these reactions ever since I ran my first Diels-Alder reaction in sophomore organic lab 50 years ago. I followed that up with dozens more both in undergraduate research (University of Minnesota, 1960–62, with W. E. Noland) and in grad school (Princeton, 1962–67, with E. C. Taylor). I guess this is my favorite reaction of all time along with other “no-mechanism” cyclization reactions. The latter would include the “ene” reaction (aka the Alder Ene reaction by J. J. Li).

I usually managed to get by on library copies of the name reactions books, but I did buy my own copy of Helmut Krauch and Werner Kunz’s “Organic Name Reactions” in grad school, which I still have. More recently I managed to review Li’s “Name Reactions,” 3rd edition.

My first love in chemistry was organic synthesis, but my second was always chemical information. Prompted by a series of information-conscious mentors, I always eagerly did my own library/information research, even during my first two post-Princeton jobs when searching services were available. When those two jobs in pesticide synthesis dried up, I was offered a position as a technical information specialist at Amoco Corp. I’ve been a chemical info specialist ever since, even in (alleged) retirement.

My primary resource was Chemical Abstracts, and I helped grow the online chemical information industry from a user standpoint. This second and lasting chemistry love is probably why I’ve always been so fascinated with the likes of name reactions. Good to see someone else still is also.

Robert E. Buntrock
Orono, Maine

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