Osmo Hormi

Formation of the mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and related compounds by chlorination of phenolic compounds

Abstract The strong bacterial mutagen, 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) was formed by aqueous chlorination of some chlorinated phenolic compounds with structures related to aromatic units in aquatic humus. Chlorination at pH 2 produced more MX than chlorination at pH 7. Compounds structurally related to MX were also determined. MX was responsible for a major part of the total mutagenicity of the chlorination products.

A Cheap One-Pot Approach to Tetraethyl Methylenediphosphonate

Abstract A cheap procedure for the preparation of tetraethyl methylene-diphosphonate is described.

A Facile Preparation of Some Furylesters

Abstract The title furans were prepared from 2(5H)-furanone 1 and chloroformates or acid chlorides without α-hydrogens in acetonitrile in presence of triethylamine in good distilled yields.

Catalytic Effect of Trialkylammonium Chlorides on the Decomposition of Enolphosphorus Dichloridates: Improved Procedure for the Preparation of β-Chloroarylidene and Alkylidene Malonates

Abstract Reaction of enolates of benzoylmalonate and phosphorus oxychloride is studied. The yield of isolated β-chlorobenzylidene malonate is doubled by using tertiary amines for the formation of the enolate of benzoylmalonate instead of starting from alkali salt. The role of trialkylammonium hydrochloride is discussed. Improved synthesis of β-chloroarylidene/alkylidene malonates is described in detail.

Reactions of the Potent Bacterial Mutagen “MX” with Nucleophiles

The potent bacterial mutagen Z-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (“MX”, acyclic form) was reacted with structurally simple nucleophiles (amines, thiol, hydroxide) and the reaction products were studied by chromatographic and spectroscopic methods. MX reacted rapidly with all the nucleophiles used. The initial reaction in organic solvents was ring opening via an acid-base reaction, followed by a nucleophilic attack on the aldehydic carbon atom. The possibility of ring opening (generation of an aldehydic function) seemed to be an important factor for the electrophilicity of MX.

An Approach to 3-Benzylfuran-2-Carboxylic Acid

Abstract 3-benzylfurfural was prepared from furfural and benzylmagnesium chloride and it was then oxidized to 3-benzylfuran-2-carboxylic acid with silver oxide in 40% overall yield.

Formation of the Potent Mutagen MX and Structurally Related Compounds by Chlorination of Phenolic Substances

Various phenols were subjected to aqueous chlorination at pH 2 and 7. The concentrations of (Z)-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid(MX) and some structurally related oxobutenoic and butendioic acids (MX-analogues) were determined. MX and the MX-analogues were formed in trace amounts. The formation was enhanced by acid conditions and in general by an increase in the chlorine dose applied. The oxidised form of the (E)-isomer of MX (ox-EMX) was formed in highest quantities of all MX-analogues at the highest chlorine dose.