The Sceptical Chymist | Scrutinizing synthesis

Published in Chemistry

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Posted on behalf of See Arr Oh who blogs at Just Like Cooking.

Ever run a new reaction, and found it doesn’t quite live up to the hype? So have I. Frustrating, isn’t it?

Back in 1921, another frustrated group — the first Editorial Board of Organic Syntheses — published a ‘slender little pamphlet’ of vouched-for preps chemists could follow. More modern variants include Nature Methods, or Prof. Alison Frontier’s compilation of notoriously touchy reactions at Not Voodoo: ‘May Require Mojo’.

In 2009, amid growing skepticism over a hydride-catalysed ‘oxidation‘, chemist Paul Docherty of Totally Synthetic repeated the experiment and live-blogged his results. This effort quickly attracted the attention of the wider chemical community — other scientists wrote in to check his results.

Blog Syn takes a page from that playbook. My initial squad consisted of Organometallica, B.R.S.M., and Matt Katcher, three synthetic chemists active in the blogosphere. We launched this blog as a collaborative effort: starting with an iron/sulfur cyclization reaction recently reported in JACS, we agreed to re-test certain reactions and pool the resulting data.

Each chemist repeated a reaction in their own lab, using their own group’s reagents, while adhering closely to the original authors’ Supporting Information. We exchanged e-mails full of tips and advice before writing the final post. As well as writing up details of the procedures and the final yields, the post was augmented with pictures of the reactions, products, and spectral data.

We dubbed this first reaction ‘moderately reproducible’, indicating isolation of correct final products, but not at the originally published yields.

We’re pretty excited about this new crowdsourcing method for checking the literature, and hope it spreads. Do you have a reaction you’ve always wondered about? Want to help further the cause, perhaps as a reaction ‘checker’? Get in touch with us on Twitter (@Organometallica, @katmatcher, @BRSM_blog, @SeeArrOh) or leave a comment on our first post.

Here’s to reproducibility!

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