55712-10-2Relevant academic research and scientific papers
Cyanoketenes. Mechanism of tert-Butylcyanoketene Cycloaddition to Aldo- and Ketoketenes
Moore, Harold W.,Wilbur, D.Scott
, p. 4483 - 4491 (1980)
tert-Butylcyanoketene cycloadds to ketene, methylketene, dimethylketene, and ethylmethyketene.The first two examples give 2-oxetanones and the last two result in cyclobutane-1,3-diones.These cycloadditions are shown to proceed by a nonconcerted dipolar mechanism involving zwitterionic intermediates.Establishment of the intermediacy of the zwitterions was accomplished by their independent generation from the thermolysis of substituted 4-azido-5-tert-butylcyclopentene-1,3-dione precursors.The mechanistic consequences of these cycloadditions and how they may apply to other ketene dimerizations are discussed.
