Publications by authors named "Jonathan A L Miles"

Fire suppression systems are known to be impacted with residual, entrained per- and polyfluoroalkyl substances (PFASs) because of historical use of aqueous film forming foam (AFFF) and fluoroprotein foam. Amphiphilic PFASs aggregate at liquid:solid interfaces creating a hydrophobic layer which reduces the effectiveness of water to remove PFAS from layered surfaces. When fire suppression systems are transitioned to fluorine free foam (F3) without appropriate cleaning, residual PFASs associated with the surfaces of the fire suppression system can contaminate the replacement F3.

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A difluorinated analogue of a ring-expanded calystegine B(2) and some N-protected species were prepared via microwave-mediated transannular ring-opening of an epoxyketone. The diastereofacial selectivity of the epoxidation reaction, which delivers the key intermediate, and the regioselectivity of the transannular reactions were analyzed by density functional theory (DFT) methods. The epoxidation stereoselectivity arises from simple steric control, whereas the ring-closure reactions are subject to thermodynamic control.

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Trifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a glycosyl phosphate.

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