Alec Todd

The synthesis and rearrangement of epoxypyrones

Abstract The oxidation of 5-acyl-4-oxo-pyran-2-carboxylic acid esters 1 , 2 to novel epoxypyrones and subsequent rearrangement to the previously inaccessible 6-substituted-5-hydroxy or 5-chloropyrones 6 - 9 are described.

s-Triazines. Part I. Synthesis and reactions of dihalogeno-heteroaryl-s-triazines

Metallated derivatives of substituted or unsubstituted furans, thiophens, and pyrroles react with 2,4,6-trichloro-s-triazine (cyanuric chloride) to produce the corresponding 2,4-dichloro-6-(heteroaryl)-s-triazines. The effect of electrophilic substitution (nitration and bromination) on such ring systems is described.

Chemistry of adamantane. Part III. The synthesis and reactions of 1,2-disubstituted adamantane derivatives

Intramolecular reactions involving reactive species (e.g., acylnitrene and oxocarbene) have been applied to effect substitution at non-activated methylene-groups to obtain 1,2-difunctionalised adamantanes. The syntheses of tetrahydroadamantano[2,1-d]pyrimidin-2-one, a number of 2H-adamantano[1,2-e]pyridazin-3(4H)-ones, and their fully reduced derivatives are also reported.

Homoadamatane methyl ketone, a novel re-arrangement product from the addition of 1-adamantyl cation to prop-2-ynyl alcohol

The addition reaction of the 1-adamantyl cation with prop-2-ynyl alcohol in conc. H2SO4 gives a rearranged product, homoadamantyl methyl ketone; evidence for its structure is presented.