Oxirans, from hydrocarbon oxidation

The selective oxidation of hydrocarbons is one of the most important chemical transformations in petroleum-based industrial processes, as the oxygenated products are used as key intermediates in organic sjmthesis [332]. The oxirane products formed from olefins are versatile products that easily undergo ringopening reactions to form bifunctional compounds. 

Notably, the Dimroth rearrangement has been shown to occur in nature with the purine and pyrimidine bases of nucleosides and nucleotides upon exposure to certain chemical entities. For example, 3,4-epoxybutene, styrene oxide and other aromatic hydrocarbon based epoxides, butadiene and butadiene monoxide, chloroethylene oxirane, chlorambucil, and acrolein, " among others, have been shown to facilitate Dimroth rearrangement, and in some cases subsequent cross-linking of DNA. While interesting from a mechanistic and biological perspective, these reactions will not be reviewed here. 

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