Common oxidants used in chemical synthesis, including newly developed perruthenates, were evaluated in the context of understanding (and better appreciating) the sensitiveness and associated potential hazards of these reagents. Analysis using sealed cell differential scanning calorimetry (scDSC) facilitated Yoshida correlations, which were compared to impact sensitiveness and electrostatic discharge experiments (ESD), that enabled sensitiveness ranking. Methyltriphenylphoshonium perruthenate (MTP3, 8), isoamyltriphenylphosphonium perruthenate (ATP3, 7) and tetraphenylphosphonium perruthenate (TP3, 9) were found to be the most sensitive followed by 2‐iodoxybenzoic acid (IBX, 2) and benzoyl peroxide (BPO, 10), whereas the most benign were observed to be Oxone (12), manganese dioxide (MnO2, 13), and N‐bromosuccinimide (NBS, 17).

With the burgeoning interest in cage motifs for bioactive molecule discovery, and the recent disclosure of 1,4‐cubane‐dicarboxylic acid impact sensitivity, more research into the safety profiles of cage scaffolds is required. Therefore, the impact sensitivity and thermal decomposition behavior of judiciously selected starting materials and synthetic intermediates of cubane, bicyclo[1.1.1]pentane (BCP), and bicyclo[2.2.2]octane (BCO) were evaluated via hammer test and sealed cell differential scanning calorimetry, respectively. Iodo‐substituted systems were found to be more impact sensitive, whereas hydroxymethyl substitution led to more rapid thermodecomposition. Cubane was more likely to be impact sensitive with these substituents, followed by BCP, whereas all BCOs were unresponsive. The majority of derivatives were placed substantially above Yoshida thresholds—a computational indicator of sensitivity.

The practice of deploying and teaching retrosynthesis is on the cusp of considerable change, which in turn forces practitioners and educators to contemplate whether this impending change will advance or erode the efficiency and elegance of organic synthesis in the future. A short treatise is presented herein that covers the concept of retrosynthesis, along with exemplified methods and theories, and an attempt to comprehend the impact of artificial intelligence in an era when freely and commercially available retrosynthetic and forward synthesis planning programs are increasingly prevalent. Will the computer ever compete with human retrosynthetic design and the art of organic synthesis?

An efficient and scalable enone-promoted method for the decarboxylation of trans-4-hydroxy-proline has been developed in flow to provide access to (R)-pyrrolidin-3-ol hydrochloride using biomass-derived isophorone.

As infrared seeking technology evolves, threats are better able to distinguish defensive infrared (IR) flares from true targets. Spectrally matched flares, which generally employc arbon-based fuels, are bettera ble to decoy some advanced missiles by more closely mimickingt he IR emission of the target. Cubanei sahigh-energyc arbon-based scaffold whichm ay be suitablef or use as af uel in spectrally matched flares.T he enthalpy of formation and strain energy of as eries of cubanes was predicted in silico, and their ther-mal and impact stability examined. All weref ound to undergo highly exothermicd ecomposition in sealed cell differential scanning calorimetry,a nd two cubanes subsequently underwentq uantitative sensitiveness testing. Despite their F of I values beingi nt he secondarye xplosive range, cubane-1,4dicarboxylic acid (F of I = 70) and 4-carbamoylcubane-1-carboxylic acid (F of I = 90) werei dentifieda sp otentially useful fuels for pyrotechnic infrared countermeasure flare formulations.Supporting information containing full synthetic, computational, and sensitivenesst esting detailsa swell as the ORCID identification number(s)for the author(s) of this articlecan be found under: https://doi.