Iodination and Iodonitration of Phenylacetylene under Solvent‐Free Conditions.

Abstract

Phenylacetylene (I) reacts with molecular iodine on grinding without a solvent for 2-10 min to give the trans-diiodide (II). The maximal yield is obtained using 2 equiv. of (I). Grinding of (I) with potassium iodide and nitric acid yields a mixture of diiodostyrene (II) and iodonitrostyrene (III), indicating that the presence of an oxidant is necessary to generate the iodonitrating agent and that iodonitrite can be formed in the absence of an organic solvent. To elucidate the role of nitrate and the nature of metal cation therein the reactions are carried out in the presence of sodium nitrate and magnesium nitrate. -(TVERYAKOVA, E. N.; MIROSHNICHENKO, Y. Y.; PEREDERINA, I. A.; YUSUBOV, M. S.; Russ. J. Org. Chem. 43 (2007) 1, 152-153; Tomsk Polytech. Univ., Tomsk 634050, Russia; Eng.) -H. Hoennerscheid 26-057