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Paper | Special issue | Vol 47, No. 2, 1998, pp.781-792
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)74
1,3-Dipolar Cycloadditions with 1-Alkoxy-substituted Nitrile Ylides

Nina Bojkova and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


Thermolysis of 4-alkoxy-1,3-oxazol-5(2H)-ones (2) (X = O) leads to reactive nitrile ylides (1) bearing an alkoxy substituent at the nitrile C-atom. These intermediates can be trapped by C,C-, C,O-, C,N-, and C,S-dipolarophiles, yielding 5-membered heterocycles via 1,3- dipolar cycloaddition. In the case of 1,3-thiazole-5(4H)-thiones (11) as dipolarophiles, two regioisomeric cycloadducts were obtained. The results of the cycloadditions are discussed with respect to the influence of the alkoxy substituent on the structure of the nitrile ylide.