The synthesis of substituted 1,4-benzoquinones, a biologically important class of compounds, was developed using μ-oxodi(phenyliodanyl) diacetate, a (diacetoxyiodo)benzene-based oxidizing reagent, in order to introduce second-year undergraduate organic laboratory students in their second semester or advanced organic students to increasingly popular and environmentally friendly hypervalent iodine chemistry. This experiment develops on concepts found in the undergraduate organic chemistry curriculum; conveniently fits into approximately two 3 h lab modules; and utilizes regularly found equipment and inexpensive, commercially available chemicals.
THE addition of pseudohalogens (for example, interest. A recent communication5 describing the INCOJ1 IN,,2 N0,Cl,3 and N021,4) to unsaturated addition of nitryl iodide (NO$) to unsaturated sugars offers an attractive method for the stereo-sugars prompts us to report some related additions specific introduction of nitrogen functions into with iodine azide (IN,). sugars and the adducts should be of considerable Iodine azide is generated i n situ by the reaction value in the synthesis of amino-sugars of biological of iodine monochloride with sodium azide in either
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