ChemInform Abstract: Diene Chlorination with Manganese Dioxide‐Trimethylchlorosilane.

Abstract

The chlorination of a variety of dienes with the title reagent to give the corresponding dichloro derivatives is reported.

Acetyl Chloride

“…198 Attempts to dichlorinate alkenes by treatment with AcCl/MnO 2 in THF, however, failed due to cleavage of THF to 4-chlorobutyl acetate. 196,199 A milder reagent that can be used to activate MnO 2 for dichlorination of alkenes in THF is Chlorotrimethylsilane. 199 Solvent for Organometallic Reactions.…”

Synthesis of Analogues of 2-iodohexadecanal, a Regulator of Iodine Metabolism in the Thyroid Gland

“…Thus, the first method is superior to the second one because the bromination reaction is regiospecific. 33 . Another chlorinating system, TMSCl/DMSO in acetonitrile, is described for the introduction of a chlorine atom into the more substituted position of a ketone 34 .…”

“…and then, diluted with brine (10 mL). The aqueous phase was extracted with CH 2 Cl 2 (3 x 10 mL) and the combined organic phases were dried, concentrated in vacuo to afford pure 1-tert-butyldimethylsilyloxy-2-mesyloxyhexadecane [33] as an oil (1.02 g, 92% 9 H), 0.88 (m, 3 H), 0.082 (s, 3 H); 0.075 (s, 3 H).…”