Triazolines from Vinyl Ethers

Organic azides combine with open-chain and cyclic eno) ethers to give A -triazolines in high yield. The addition is stereospecific cis and the orientation process is determined by electronic effects.145-160 The triazolines are unstable above 100° and can decompose in mainly two ways. 44 Triazolines from the open-chain enol ethers, vinyl butyl ether, /S-ethoxypropene, and a- and /3-methoxystyrene, eliminate alcohol thermally and are converted into 1,2,3-triazoles. For example, the triazoline 67 from /J-ethoxypropene 66 and p-nitrophenyl azide decomposes quantitatively at 150° into l-(p-nitrophenyl)-5-methyl-1,2,3-triazole (68). 

His research contributions to polymer chemistry span many areas, from studies of alternating copolymers of maleic anhydride and vinyl ether ( pyran copolymer ) having interferon inducing capability and antitumor activity, to polymerization of triazoline diones and synthesis of the antiaromatic 3,3-dimethoxycyclopropene. 

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