Name reactions: how does the label stick?

Organic chemistry is famous among university students for its long lists of ‘name’ reactions: Diels–Alder, Claisen, Wittig and so on. People in other subjects often gain the impression that the course consists mostly of committing these to memory, rather like memorising the names of bones and muscles in an anatomy class. Admittedly, many organic students (the less thoughtful ones) have worked their way up to a substandard grasp of the field by doing just that and little else. But such reactions are not named as they are for this reason.

Indeed, it’s not like there is some sort of International Named Reaction Committee meeting once a year in Zurich (although that does sound like a nice sideline, with plenty of opportunities for shadowy extra income).

How does it happen? Some of these names go back to the 19th century, and many more of them come from the first decades of the 20th. Once in a while, I wonder if the tradition is dying out. Are we still naming reactions after their discoverers?

My guess is that the whole practice started because organic synthesis was not yet on a firm mechanistic footing, which could make some reactions seem like isolated phenomena. Without a systematic way to categorise things at a molecular level, reactions picked up common names in the way that birds or plants had. As it became possible, names were attached more descriptively: instead of the Whoozat Reaction, you would be more likely to have the Whoozat Oxidation or the Whoozat Rearrangement. (Outside this scheme, though, there are names that have become attached to compounds, rather than to their reactions – the Whoozat reagent or Whoozat catalyst.)

What was necessary shorthand for referring to reactions (at least at that time) was also a mark of respect. Since then, names have stuck for reactions that are unusual or useful, ones that are, in other words, worth remembering. Look at the other end of the scale: there must be a hundred ways in the literature to dehydrate an oxime to a nitrile, and how many of them have a name? And who would bother to remember them if they all did?

Perhaps that should read ‘were unusual’, instead of ‘are unusual’. One of the most common reactions in organic chemistry is the formation of an ester from an acid and an alcohol with a bit of acidic catalyst. Fischer was the man who first codified this, though, and Fischer esterification is a useful enough procedure that I did one just this week.

Are we still doing this? Not, perhaps, at the rate that we were decades ago, even though the organic chemistry literature is larger than ever. The sheer mass of known transformations means that it is harder to come up with new and memorable ones. But my impression is that naming reactions (or reagents) for their discoverers is still very much a living tradition, provided you manage to get over the ever-rising threshold. In the last 25 years, I think the majority of names have been attached to metal-catalysed transformations, which is fitting, considering their impact. Grubbs, Suzuki, Buchwald–Hartwig – the names are still out there.

So if you come up with a great, new reaction that does something people want to get done, it may well be named after you. But if this is your goal in life – and there are worse – then you still have a few considerations to keep in mind, besides that little discover-a-great-new-reaction step. You should definitely publish a number of papers defining and extending your new chemistry, rather than trusting others to find out how great it is. You should go to high-profile conferences and meet people to spread the word. Getting commercial vendors to sell any special reagents needed is a good idea, too. And while you’re at it, you might want to avoid giving any of those items catchy acronyms because those could easily end up as the chemical world’s favoured mnemonic instead.

Nothing is for certain in this world, though. Despite the number of reactions (and publications) HC Brown generated, none of his hydroborations ended up named after him. Perhaps you don’t want your last name to be an adjective!