Cornelis Moorhoff

Synthesis of Acyclic, Symmetrical 3,3′-Allyl Dithioethers, from the Alkylation of 3-Mercapto-2-mercaptomethylprop-1-ene in the Presence of Sodium Hydride

A novel method where 3,3′-allyl dithioethers have been prepared from 3-mercapto-2-mercaptomethylprop-1-ene and two mol equivalent of alkyl halide in the presence of two mol equivalent of sodium hydride has been developed. Using this method, bisepoxide, 2,2′-(2-methylenepropane-1,3-diyl)bis(sulfanediyl)bis(methylene)dioxirane (8) has been synthesized from epichlorohydrin, whereas potassium carbonate was unable to deliver this product. These 3,3′-allyl dithioethers can be utilized either as monomers, or with further chemical reactions transformed into more complex monomers, for photoplastic polymer networks.

Synthesis of Symmetrical, Substituted (alkane-α,ω-diyl)(bis[3,3′-allyl dithioethers]) Monomers for Photoplastic Polymer Networks

Novel symmetrical (alkane-α,ω-diyl)(bis[3,3′-allyl dithioethers]) compounds and their ether analogues, have been synthesised from (alkane-α,ω-diyl)bis([2-{chloromethyl}allyl]sulfane) precursors, for use in crosslinked polymers which exhibit photoplastic behaviour. Facile synthesis and purification of these monomers was achieved if the alkane-α,ω-diyl moiety had at least one oxygen atom in this linker. The number of sulfur atoms in these monomers was varied from four to two to zero to produce monomers which can be used to evaluate their importance on the photoplasticity behaviour.

Toward preparative resolution of chiral alcohols by an organic chemical method

Asymmetric alcohols were resolved as 1-α-O-alkyl-2,3-unsaturated hexosides. After separation of diastereoisomers, the auxiliary and the enantiomeric alcohol were recovered by transglycosidation. Potential applications include resolution of labile secondary and tertiary alcohols, difficult by existing techniques, and enhancement of ees of chiral alcohols produced enzymatically or by synthetic catalytic methods.

Transformation of substituted 2H-pyran-5-carboxylates into 3R*-vinyl-1,2R*-cyclopropanedicarboxylates

Substituted alkyl 2H-pyran-5-carboxylates, 1, have been condensed with methyl 2-(triphenylarsoranylidene)ethanoate, 14a, to form substituted 3-vinyl-1,2-cyclopropanedicarboxylates, 15, and, in a number of cases, 2,3-dihydro-3-vinyl-2,4-furandicarboxylates, 16. NMR experiments showed that for the majority of cyclopropane products formed, the cyclopropane ring hydrogen atoms have the trans configuration. This was validated by molecular orbital calculations. Biological screening tests revealed that these compounds showed some ectoparasiticidal activity.

Preparation of liquid substituted benzoyl peroxide mixtures

A series of alkyl substituted benzoyl peroxide mixtures were synthesised from two or three acid chloride combinations in aqueous sodium peroxide and butanone solutions to form liquid benzoyl peroxide mixtures.