An experimental and computational investigation is conducted into the role of substituents in retro Diels–Alder extrusion of CO2 from 2-oxa-bicyclo[2.2.2]oct-5-en-3-ones. We provide the first experimental evidence that loss of CO2 from the cycloadducts significantly depends on the nature and position of the substituents. For example, we show that whilst 5-carboethoxy-2-pyrone undergoes a more facile cycloaddition that 3-carboethoxy-2-pyrone, the cycloadduct from the latter pyrone undergoes a more facile loss of CO2 than the cycloadduct from the former pyrone.

A general method for the synthesis of a novel class of oligomers, comprising α-hydroxy phenylphosphinic acid building blocks, is reported. A series of dimeric α-hydroxy phenylphosphinates are analyzed by a combination of NMR spectroscopy, X-ray crystallography and computational methods.

A general synthetic methodology for the synthesis of sugar-carbasugar pseudodisaccharides is described. The methodology is based on the cycloaddition of pyran-2-ones to vinylated sugars and the subsequent manipulation of the cycloadducts to construct the carbasugar component of the pseudodisaccharide.

A general method for the synthesis of a novel class of oligomers, comprising α-hydroxy phenylphosphinic acid building blocks, is reported. A series of dimeric α-hydroxy phenylphosphinates are analyzed by a combination of NMR spectroscopy, X-ray crystallography and computational methods.