A one-step copper-catalyzed reaction of aldehyde-derived N-substituted hydrazones with CCl4 resulted in efficient synthesis of 4,4-dichloro-1,2-diazabuta-1,3-dienes. It was proven that this C–C bond-forming cascade reaction operates via an addition of trichloromethyl radical to the CN bond of hydrazone followed by a base-induced elimination of HCl. The reaction was found to be very general, as diverse hydrazones possessing various aromatic groups at N-site, as well as aromatic, aliphatic, and heterocyclic substituents at C-site, are capable partners for coupling with a wide range of polyhalogenated compounds (CCl3Br, CBr4, CCl3CN, CCl3COOEt, CCl3CF3, CBr3CF3) to produce a family of functionalized 1,2-diazabuta-1,3-dienes. It was demonstrated that the prepared heterodienes are highly versatile building blocks for straightforward assembly of various valuable acyclic and heterocyclic molecules.

The toxic effect of strained hydrocarbon 2,2'—bis (bicyclo[2.2.1]heptane) (BBH) was studied using whole-cell bacterial lux-biosensors based on Escherichia coli cells in which luciferase genes are transcriptionally fused with stress-inducible promoters. It was shown that BBH has the genotoxic effect causing bacterial SOS response however no alkylating effect has been revealed. In addition to DNA damage, there is an oxidative effect causing the response of OxyR/S and SoxR/S regulons. The most sensitive to BBH lux-biosensor was E . coli pSoxS-lux which reacts to the appearance of superoxide anion radicals in the cell. It is assumed that the oxidation of BBH leads to the generation of reactive oxygen species, which provide the main contribution to the genotoxicity of this substance.

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The Type-A photochemistry of cyclohexadienones is well-studied and follows a well-established mechanistic pathway. One early example is the rearrangement of santonin to lumisantonin. Another example is the rearrangement of 4,4-diphenylcyclohexa-1,5-dienone. Remarkably, replacement of one carbon by nitrogen alters the reaction course to give a regioselective phenyl migration.

We report a synthetic scheme for obtaining new spiro-hydrocarbons from a versatile norbornane derivative, methylenenorbornane. As a result, four new spiro-hydrocarbons and the isomeric-related norbornanes for the comparison have been obtained in moderate or good yields through [4π + 2π] and cyclopropanation reactions. The effect of introducing a spiro-center is dependent on the nature of carbocycles at a spiro-carbon atom. There is no obvious advantage in properties for spirocycloalkenes consisting of norbornane and cyclopropane rings at the spiro-carbon atom compared to isomeric hydrocarbons. At the same time, spirocycloalkenes with two norbornane motifs at a spiro-center have exhibited much higher values of densities and energy densities (0.992–1.023 g/mL, 41.79–43.28 MJ/L) than the related hydrocarbons without a spiro-center and JP-10. The obtained results can provide insight and an opportunity to further expand this work to bring new high-performance jet fuels to market.

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