Mark Bernard Yunker

Anomalous oxidative dimerisation of some carbohydrate primary alcohols with CrO3,2C5H5N

The hydroxymethyl group of some carbohydrate molecules undergoes oxidative dimerisation with CrO3,2C5H5N, there being no evidence of an intermediate aldehyde having formed prior to the dimerisation.

Pyrano-sultone: a novel binuclear heterocyclic system

Reaction of the α-keto alcohol (1) with MeSO2Cl–Et3N–CH2Cl2 gives, in addition to the keto sulphonate (2), the unsaturated sultone (3) the relative amounts of which vary with temperature; when pyridine is the proton acceptor, the sultone is not formed, and hydrogenation gives the saturated sultone (5) exclusively.

Ground and excited state 1,4-addition reactions of some carbohydrate enones

Highly functionalised branched-chain monosaccharides can be prepared by sensitised irradiation of conjugated enones (1) and (2) in an alcohol whereupon equatorial 1,4-addition of the carbinol is the major event, the adducts so obtained being correlated with the products of ground-state additions.