91930y Interaction of carbonyl compounds with organometallic azides. V. Sorboyl chloride and its conversion to an alpha-pyridone. MacMillan, John H.; Washburne, Stephen S. (Dep. Chem., Temple Univ., Philadelphia, Pa.). J. Org. Chem. 1973, 38(17), 2982-3 (Eng).

Electrocyclic ring closure of alpha,beta-cis1,3-pentadienyl isocyanate affords 3-methyl-2(1H)-pyridone in fair yield. The isocyanate is formed in good yield by treatment of sorboyl chloride with trimethylsilyl azide in refluxing toluene. In refluxing heptane this reaction affords tetrazolinone 1 rather than isocyanate. The sensitive pentadienyl isocyanate is converted to polymer by either pyrolysis or acid treatment. Chem Abstr. Vol 79, 91930y.

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