Date of Award
Doctor of Philosophy (PhD)
Professor J. Warkentin
A new approach to the synthesis of 3,3-dialkyloxindole systems which involves reaction of a dialkyldiazomethane, generated (in situ) by the thermolysis of a 5,5-dialkyl-∆³-1,3,4-oxadiazolin-2-one, with an aryl isocyanate, has been developed. Minor products of the reaction are a 2-imino-5,5-dialkyl-4-oxazolidone and a 5,5-dialkylhydantoin. The synthesis of both a 2-imino-5,5-dialkyl-4-thiazolinethione and a 5,5-dialkyl-2,4-dithiohydantoin has been achieved in a similar manner, using phenyl isothiocyanate in place of phenylisocyanate. Spectroscopic data, in particular ¹³C chemical shifts, and chemical transformations are cited in support of the structural assignments. Possible mechanisms for the formation of the heterocyclic compounds are considered.
Fulton, Janet Barbara, "The Reaction of Diazoalkanes with Heterocumulenes. Mechanism and Synthetic Utility" (1978). Open Access Dissertations and Theses. Paper 692.