1. What made you want to be a chemist?
When I was 12 or 13, I met William Doering. I had asked/demanded (remember I was all of 12) of my parents to be allowed to play the 12-year old tennis circuit that summer. My parents properly replied, “Time to get a job, kid.” They met Doering at a party and coerced, or bribed, him into giving their kid what would today be called an internship at Hickrill, a privately funded basic research lab that happened to be near where we lived. There I not only met Doering, for whom I would work for the next ten years or so, but several other wonderful organic chemists, including Larry Knox, for whom I directly worked at Hickrill, washing dishes and being a general gopher. I knew nothing, of course, but the atmosphere was electric, the work intense, and the passion palpable. No one with the slightest interest in science could emerge from that place unchanged.
2. If you weren’t a chemist and could do any other job, what would it be – and why?
All my life I have loved jazz, and I have spent an enormous number of hours in dingy clubs over the last five or six decades. I know a lot about the music and run a jazz series in Princeton, New Jersey. I probably – certainly – could not be a musician, but I could run a club, or maybe be a critic. I still might do that.
3. What are you working on now, and where do you hope it will lead?
Well, I closed the research lab when I moved from Princeton to NYU, so I can only answer that in retrospect. My group worked on the chemistry of reactive intermediates, carbenes, benzynes, and the like. We also expanded into the chemistry of boron cage compounds, and the interactions of reactive intermediates with those three-dimensionally aromatic compounds. We hoped only that it would lead to a better understanding of how molecules react – and of how “electrons talk to each other.”
4. Which historical figure would you most like to have dinner with – and why?
Thelonious Monk. I saw and heard Monk when I was a kid. Indeed, I was at the Five Spot for a few of the times Monk played with John Coltrane. I didn’t have a good enough understanding of the music then, and I’d like to talk to Monk about his music, or, better, to see him play again, nowI have a deeper appreciation of it.
5. When was the last time you did an experiment in the lab – and what was it?
A long long ago, probably in the 1970’s – or even 1960’s. Peter Gaspar was visiting Princeton for a semester, and we happened on a result of Bill (Florida) Jones’s that had, we thought, important implications for the chemistry of phenylcarbenes. So I ran the experiments, evaporating p-tolyl diazomethane through a hot pyrolysis tube and collecting the products, styrene and benzocyclobutene, as Peter and I expected/hoped. Write it out – it is a remarkable transformation. Then work out a mechanism. It’s wonderful chemistry. It turns out that a student of Harold Shechter’s had run similar experiment but for some reason Harold never published them at the time and they languished in Dissertation Abstracts.
6. If exiled on a desert island, what one book and one music album would you take with you?
It has to be a book I’ve read because one can’t take chances on a desert island, so I might pick Thomas Pynchon’s Gravity’s Rainbow, for sheer flat-out virtuosity. Even if one doesn’t get all the references – or even if one doesn’t get the point at all – one can read it page by page, sentence by sentence, just for the brilliancy of the writing. And it’s long. If I am allowed another, I’d take David Foster Wallace’s Infinite Jest – for much the same reasons. Or maybe Vikram Seth’s A Suitable Boy. Or….
Music is easy: Charlie Parker, the Collected Dials and Savoys.
7. Which chemist would you like to see interviewed on Reactions – and why?
There are only a small number of the great physical organic chemists left – Doering and Roberts, I guess. Few know them now, I’m afraid, as the discipline has fallen so far out of favor. It would be nice to let them have a chance to make the case again.