John G. Dingwall

1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described. These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrqsine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved. Tha alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties. Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkyl-phosphonic acid analogues of (±)-alanine, (–)-alanine, (±)-valine, (–)-valine, (±)-serine, (±)-threonine, (±)-lysine, (–)-leucine, and (±)-ornithine.

New carboxyphosphonic and phosphinic acid structures of technical and biological interest

Abstract Carboxyphosphonic and phosphinic acids have recently found applications in the diverse fields of industrial water treatment and pesticides. For example, the acids 1 and 2 are ferrous corrosion inhibitors and scale control agents for circulating industrial water systems, the amino acid 3 is a translocateable total herbicide and the naturally occurring glutamic acid analogue 4 has antibacterial, fungicidal and herbicidal properties. This paper presents a selection of our results on the synthesis of new carboxyphosphonic and phosphinic acids which led to corrosion and scale control agents and structures related to natural products, and their postulated biogenetic precursors.

Free radical catalysed additions to the double bond of diketene: a synthesis of novel oxetan-2-ones

Free radical-catalysed additions to the exocyclic double bond of diketene are described. Thiols give unstable 4-thiomethyloxetan-2-one adducts which could be oxidised to their more stable sulphoxides or sulphones. Addition of a range of P–H compounds led, with a few exceptions, to stable phosphorus-substituted 4-methyloxetan-2-ones. The radical-catalysed chlorination of diketene by sulphuryl chloride has been shown to give 4-chloro-4-chloromethyloxetan-2-one. Further 4-halogeno-oxetan-2-ones were prepared by addition of halocarbons such as carbon tetrachloride, bromotrichloromethane, and carbon tetrabromide and of trichloromethanesulphenyl chloride to diketene.

Organische phosphorverbindungen. LXXXVI: Herstellung und Eigenschaften von ϖ-phosphinyl-α-aminoalkyl-Carbonsäuren

Abstract The synthesis, chemical and spectral properties of ω-methylphosphinyl-α-aminoalkylcarbonic acids, CH3 (HO)P(O)(CH2)n CH(NH2)CO2H, n=3, 4, 5 or 6, are described. In contrast to the corresponding phosphonic acid derivatives these compounds exhibit no anticonvulsive and NMDA-antagonistic properties.

NITRIC ACID OXIDATION OF 3-PHOSPHONO-3,5,5-TRIMETHYLCYCLOHEXANONE

Abstract Ammonium metavanadate catalysed nitric acid oxidation of 3-phosphono-3,5,5-trimethylcyclohexanone 1 gave a mixture of the three dicarboxylic acids 2, 3 and 4 which were characterised by isolation (2) or synthesis (3,4).