6533b839fe1ef96bd12a652a

RESEARCH PRODUCT

Nebenreaktionen der radikalisch ausgelösten Cyclisierung von 2,2′-Methylen-bis(4-methyl-1,2-phenylen)-dimethacrylat

Hermann KämmererJiri Pachta

subject

Mole ratioPolymers and PlasticsChemistryHead to headMethacrylateMedicinal chemistrychemistry.chemical_compoundColloid and Surface ChemistryColumn chromatographyPolymerizationYield (chemistry)Polymer chemistryMaterials ChemistryProton NMRPhysical and Theoretical ChemistryBenzene

description

2,2′-Methylene-bis(4-methyl-1,2-phenylene) dimethacrylate (1) was reacted with an excess of 2,2′-azoiso-butyronitrile (mole ratio 1:15) highly diluted in boiling benzene. The reaction products were separated by column chromatography. It was found that the 1-cyano-1-methylethyl radical induced the cyclization of 1 to yield the product of a head to tail addition (2) in 55% yield. In addition, the product of a head to head addition (3) was isolated in 4% yield. 35% of 1 reacted in the same way as it has already been observed as suppression of polymerization in the case of p-tolyl methacrylate to give the products 4 and 5. The structures of the products were confirmed by elemental analyses, by IR-UV-, 1H NMR- and mass-spectra as well as by the determination of their relative molecular masses and by quantitative hydrogenations.

https://doi.org/10.1007/bf01521591