3 We took a step back by placing the speakers inside the fume hood, which was meet with an increase in yield. This was ineffectual, as the speakers rapidly dissolved in the solvent, giving a mixture measuring in at 9 on the Browning Index. Initially, we took this idea to the extreme by suspending small speakers in the reaction mixture. Starting with a measly 20% yield for a reaction catalysed by the lab stereo, we postulated that bringing the music source closer to the reaction would amplify the effect. Figure 1 shows a selection of techniques tested, with the yield of 2 as a model system. Our first task was to find a more efficient way to introduce sound into our reactions. Intrigued by the potential of this new field of echocatalysis to help us stick one to Phil Desolate, we chose to investigate further (in the hopes that we can commercialise it). For a more complete control experiment, we used John Cage’s 4’33’’ For example, “Smoke on the Water” and “Feel Good Inc.” produced good yields of 2, while Vivaldi’s “Four Seasons” gave only trace amounts of product. We tested a number of classic songs and ascertained that a strong bass line was essential to initiate the Grignard reaction (scheme 1). Some further investigation eliminated the first explanation: Shia Labeouf’s “just do it” talk was completely ineffective while “bangarang” initiated the reaction. We hypothesised two explanations for this effect: 1) This absolute banger was capable of providing motivation on a molecular level, or 2) thumping bass was eliciting an effect similar to sonication and helping to dislodge the oxide layer from the Mg turnings. Playing Bon Jovi made Pete’s Grignard reaction work better. Resigned, he set the reaction up again, only to encounter the same lack of reactivity, and the same solution. Returning to work on Monday, Pete discovered that his reaction was now an ethereal suspension of magnesium hydroxide, as he had left it stirring under house-nitrogen 2 for the whole weekend. Then he went to the pub and forgot all about it. Perplexed, Pete pondered if pounding pop-songs had prompted his product to proliferate. On his final paranoia-suppression walkaround, he noticed that his Grignard reaction was merrily boiling away. While blasting out the lyrics to this classic cleaning-up song, Pete shut down the lab. Should have known better than to do this on a Friday-avo.” He returned to his mountain of dirty glassware, pausing only to queue up “Livin’ on a Prayer” on the stereo and max the volume. Exasperated, our hero exclaimed “Well fuck it then, guess this is a Monday-Pete problem.
More iodine elicited no response, so he tried Br 2, then TMSCl, then dibromoethane, then heating and finally abuse, all without effect. Pete added a pinch of iodine, while checking the time furtively. Just as he began washing up, he noticed that the reaction had not initiated. Earlier in the afternoon, he’d set up a Grignard reaction (the old-fashioned way), hoping to dump in his electrophile at 5 pm and bugger off down the pub. Pete was rushing to finish his lab work, hoping to make it to the biannual West Failure trivia night at The King’s Kneecap. Like so many good stories, this one begins on a Friday afternoon. Unfortunately, sonochemistry already exists, so we’re using music instead and calling it “echochemistry”. We defiantly can’t beat them, so we’ve developed our own iteration of this copy-catalysis by exposing chemical reactions to sounds. However, pointing this out doesn’t change the fact that we have to compete with these people for grants. It might be a mechanochemically generated Grignard reagent, an electrochemical Birch reduction, a lithiation in flow, a photocatalytic halogenation or even an organocatalytic Suzuki coupling. More specifically, they are finding new ways of doing the same reactions they were doing 20 years ago, with a twist. Pete Tcharkovsky, A Freddy Chopin, A Johnny Strauss, A Eddie Greig, Jimmy Puccini, A Archduke Metallica A and Günther Schlonk B*Ībstract: Chemists are constantly pushing the boundaries of synthetic methodology.
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