(Dicyano)iodonium triflate- novel iodonium species and a versatile reagent for the preparation of iodonium salts via an iodonium transfer reaction with organostannanes
✍ Scribed by Peter J. Stang; Viktor V. Zhdankin; Rik Tykwinski; Nikolai S. Zefirov
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 227 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In recent years a large variety of polyvalent iodine compounds have &come available, and theit versatility in organic synthesis has been well establishedI. Of special synthetic interest are iodinetII1) derivatives with one or two cyano ligands covalently attached to the iodine atom2, The recently reported phenyl(cyano)iodonium salt& have been found to be valuable reagents for the preparation of various alkynylj and alkeny14
(phenyl)iodonium sprcies via a novel iodonium transfer reaction with the corresponding organolin derivatives.
In this paper we wish to report the preparation of a new cyanated iodinanc, (dicyanniononium) triflate 3, and its application as a versatile reagent for a mild in situ synthesis of various; iodonium triflate salts. Compound 3 can be prepared by the reaction of iodosyl tritlate 15 with trimethylsilyl cyanide in methylene chloride at -2OoC. Addition of cold hexane to this solution results in the precipitation of colorless crystals which can be isolated in 40-60% yield by filtration at -7XoC under nilrngen. Crystalline 3 completely decomposes at room temperature in 2-5 min with the formation of cyanngcn iodinr. I(IN, as the only isolable stable product. Compound 3 is air-sensitive and it' the filtered crystals are expnsed to air an explosion may occur. It can however be stored at -2W: under nitrogen for several days.