Iodination and iodo-compounds. Part III. Iodination of some aromatic nitro-compounds with iodine in 20% oleum

Abstract

The use of iodine in 20% oleum for the iodination of a range of aromatic nitro-compounds is described. The conditions necessary to achieve reaction and proof of the identities of the products are included. The system has been found to behave as an electrophilic reagent but it will not introduce an iodine atom ortho to a nitro-group.Technology, Romford Road, London E.15 THE direct iodination of aromatic molecules containing deactivating substituents has received little attention. Suitable reagents are those involving cationic iodine in concentrated sulphuric acid or oleum. Iodine in 50-65% oleum,2 in which the electrophile is probably3 12+, has frequently been used to polyiodinate singly and double deactivated molecules, but it is difficult to use for partial iodination under controlled conditions, as the reaction mixture usually has to be heated to remove the 1

Thermodynamic contribution of iodine atom to the binding of heterogeneously polyhalogenated benzotriazoles by the catalytic subunit of human protein kinase CK2

“…1,2‐diiodo‐4,5‐dinitrobenzene was obtained from 1,2‐dinitrobenzene according to procedure described by Youngblood . Iodinating agent in this reaction is I 3 + , which forms from iodine in oleum . Reduction with tin(II) chloride dehydrate allowed to obtain 1,2‐diamino‐4,5‐diiodobenzene.…”

Crystal Engineering with Symmetrical Threefold Acceptor-Substituted Triaminobenzenes

“…m.p. ); 1 H NMR (CD 3 CN) no signal; 2,4,6-Trichloro-3,5-dinitroaniline (25): [51] A solution of 3,5-dinitroaniline [52] ( 3,5-Dinitroiodobenzene (27): [53] M.p. 100.5 ± 103 8C, then recrystallizing and melting at 104.5 ± 105.5 8C (first from EtOH, then from n-heptane/toluene), lit.…”

Iodination of nitroarenes by a superactive reagent based on iodine chloride

“…After two hours, the reaction mixture was treated as described in method A to give compound 9b (109 g, 37%), m.p 97--9,8 ~ (PriOH) (Ref. 4:99--11)0 ~…”