By A. Varvoglis
This ebook describes the interesting chemistry of the numerous varieties of natural compounds of hypervalent iodine. every one bankruptcy bargains with a selected iodine compound or households of compounds that have been used as reagents in a plethora of worthwhile alterations. those comprise diverse oxidation, similar to with the valuable Dess-Martin reagent in addition to with quite a lot of extra reactions.Prominent beneficial properties of hypervalent iodine reagents derived from iodobenzene are: prepared availability, operational simplicity, light response stipulations, and excessive potency. they're environmentally secure and will be recycled. New species could be simply ready by means of introducing substituents within the benzene ring or altering the ligand hooked up to iodine. Their blend with different reagents broadens significantly their artificial strength. this present day, no artificial chemist can find the money for to disregard the precious hypervalentiodine reagents. Key positive aspects* good points updated insurance of a variety of subject matters* contains many tables that includes a range of reactivity, and a accomplished index* Acts as a entire, up to date reference on all points of hypervalent iodine chemistry* incorporates a part on strange potency of hypervalent iodine reactions
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Additional info for Hypervalent Iodine in Organic Synthesis (Best Synthetic Methods)
It is emphasized that most preparations are very convenient, so that it is not necessary to purchase commercially available compounds; these and their suppliers include: (Diacetoxyiodo)benzene: Aldrich, Fluka, Lancaster, Merck [Bis(trifluoroacetoxy)iodo]benzene: Aldrich, Fluka [Bis(trifluoroacetoxy)iodo]pentafluorobenzene: Aldrich, TCI America Iodosobenzene: ICN, TCI America 2-Iodosobenzoic acid: Aldrich, Fluka [Hydroxy(tosyloxy)iodo]benzene: Aldrich Diphenyliodonium-2-carboxylate: Lancaster Diphenyliodonium chloride, bromide, and iodide: Aldrich, Lancaster Perfluoroalkyl phenyliodonium salts: TCI America Because of the multitude and diversity of iodonium salts and zwitterions, some of which are labile or are prepared for specific purposes, their preparative methods are discussed in Chapter 8, for diaryl iodonium salts and related compounds, Chapter 9 for perfluoroalkyl, alkenyl and alkynyl phenyliodonium salts and Chapter 10 for zwitterionic iodonium compounds.
Hydrofluoric acid (48%, 10 ml) was added and the bottle shaken vigorously for about 1 min. The colour of the solution turned from bright yellow to nearly colourless. Then the solvent phase was carefully decanted. The residue was shaken with dichloromethane (50 ml) which was combined with the original solution. The reagent formed was used in this solution for fluorination. In order to find its titre, a portion (1 ml) was analysed by titration of the iodine liberated by reaction with aqueous potassium iodide.
2 Amides and hydrazides Amides of carboxylic and other acids react with DIB in various ways. Simple primary carboxamides, RCONHz, and also peptidamides, undergo a facile Hofrnann-type rearrangement affording amines with one less carbon atom. 1). A high yield preparation of urethanes was reported from amides and DIB in methanolic potassium hydroxide : DIB MeOR KOH 70-97% RCONH2 -- RNHCOOMe A related reaction accompanied by cyclization occurred with ortho-substituted benzamides (and also non-cyclic amides such as RCH(CONH2)2 .
Hypervalent Iodine in Organic Synthesis (Best Synthetic Methods) by A. Varvoglis