
%0 Journal Article
%A Hanhela, PJ 
%A Paul, DB 
%T Synthesis and Stability of Aryl Bis(nitrile oxides) With Potential as Curing Agents for Polysulfide Sealants
%J Australian Journal of Chemistry
%D 1989/02/01
%V 42
%N 2
%P 287-299
%K 
%R https://doi.org/10.1071/CH9890287
%U https://www.publish.csiro.au/paper/CH9890287 
%X Several aromatic bis( nitrile oxides) have been prepared as potential curing agents for sealants produced from thiol -terminated polysulfide liquid polymers. All were obtained by dehydrohalogenation of &#945;-halo oximes and the requisite aldehydes were synthesized from either the dimethyl derivatives or the chloromethylated hydrocarbons. The direct chloromethylation of naphthalene which offered a convenient route to the naphthalene-1,4- and 1,5-bis(carbonitrile oxides) was re-examined. Also prepared were naphthalene-2,6-bis(carbonitri1e oxide), anthracene-9,10-bis(carbonitri1e oxide) and 4,4&#8242;-sulfonylbisbenzonitrile dioxide. The course of the reaction between naphthalene-2,3-dicarbaldehyde and hydroxylamine was established and shown to differ from that involving phthalaldehyde. Stabilities of the nitrile oxides at -15º, 4º and 25º were assessed by spectroscopic means. 
