Reactions – Ian Fleming

Ian Fleming is an Emeritus Professor in the Department of Chemistry in the University of Cambridge, and worked on a range of topics in the general area of synthetic organic chemistry. He is best known as a pioneer in applying organosilicon chemistry to control the regio- and stereo-chemistry of a variety of organic reactions.

1. What made you want to be a chemist?

A short answer is: because it was transparently interesting. But it is much harder to identify why I found it so. When I was eleven or so, I had a chemistry set – an almost useless one – which I augmented with purchases from a chemist’s shop over the road from my school, with a Bunsen burner, conical flasks, glass tubing, funnels etc., and with a few items my father brought home from his work as a metallurgist, like copper sulfate, and concentrated hydrochloric and sulfuric acid. The first few years of school chemistry seemed to me obvious. The chemistry master, Mr Timbrell, had written an excellent book with the School Certificate syllabus in it; I read it, understood it and remembered it. I repeated what I could of it at home, and at school sat at the back of the class playing chess while he droned on and on. The subject really came alive when we got to organic chemistry in the sixth form, taught by Stan Featherstone, who arranged for me to stay after school and carry out experiments from Mann and Saunders’ textbook. I had made about 50 organic compounds by the time I left school, more than all the ones I made as an undergraduate, so I was an experienced practical chemist early on. My other subject was biology, which I fully expected to be a part of my career, but when I met biochemistry at Cambridge I soon realised that the only part I found interesting was metabolic pathways – the chemistry. At the same time, in my second year, we met organic reaction mechanisms, first from Peter Sykes and then more compellingly from Malcolm Clark, and molecular orbital theory from Christopher Longuet-Higgins. The subject began to have a satisfying intellectual structure, and I was hooked. From then on, and especially in the next four or five years, I was able to order all my organic chemical knowledge into a coherent framework, to which I’ve been adding all the time. So a second short answer is: Stan Featherstone, Malcolm Clark and Christopher Longuet-Higgins.

2. If you weren’t a chemist and could do any other job, what would it be – and why?

Realistically, of course, I would have been something close to a chemist: a biochemist or even maybe a doctor, but that is not interesting. Moving away from science, and choosing something from within my competence, I might have liked to be a photojournalist, because you get to see extraordinary things and people. I might equally have answered a film director, if I were allowed to interpret the words “could do” in the question to mean that I had magically been given the talent.

3. What are you working on now, and where do you hope it will lead?

I am rewriting my textbooks – I’ve finished and published the sixth edition of the Spectroscopic Methods book that Dudley Williams and I wrote, and am now putting the finishing touches to two versions of a book to replace my Frontier Orbitals book, which is now an astonishing 33 years old. I have a 300-page “student” edition at the same level as the Frontier Orbitals book, and a 550-page “library” version, with all the references and much more material, for those who want more. As before, it treats the subject without mathematics for the benefit of all those organic chemists like me who have little mathematical aptitude but want to understand the subject in a physical way. The new versions will be called Molecular Orbitals and Organic Chemical Reactions, with less emphasis on the Frontier Orbitals. My next task will probably be to look again at an even older book of mine: Selected Organic Syntheses.

4. Which historical figure would you most like to have dinner with – and why?

Samuel Johnson was arguably the wisest man ever, and good company. But a great many other names come to mind: Queen Elizabeth I, Henry James, Virginia Woolf, Orson Welles, Shakespeare, Billy Wilder? What a dinner party.

5. When was the last time you did an experiment in the lab – and what was it?

Some of my later co-workers may remember my showing them how to get crystals – a lost art it seems, but I don’t think that counts as an experiment. The last preparation I remember was the preliminary work for the indole syntheses that Mike Woolias developed, when I prepared the way for him, by establishing that the reaction worked. It involved an amino group displacing an aryl halide, long before Buchwald and Hartwig, and without any transition metals being necessary. I remember leaving a reflux going to open an epoxide with benzylamine in ethanol, while I went to the Oxford Synthesis Meeting in July 1973, and coming back to find that not only had the epoxide been opened but the intramolecular displacement of the ortho bromide had also taken place.

6. If exiled on a desert island, what one book and one music album would you take with you?

It’s always difficult to restrict oneself to one. It would have to be big. War and Peace, perhaps, or is one allowed the whole of Shakespeare? For music, it would have to be the late Beethoven quartets.

7. Which chemist would you like to see interviewed on Reactions – and why?

David Evans of Harvard, because he is inspirationally thoughtful in teaching and research.