N-iodo succinimide

Succinic acid, 2,2-difluoeo-, 42, 44 SuCCINIMIDE, N-IODO-, 42, 73 Sulfonation of pyridine, 43, 97 Sulfur tetrafluoride, in conversion of carboxylic acids to 1,1,1-trifluoro compounds, 41, 104/ toxicity of, 41,105 / ... 

Thallium(I) benzoate Benzoic acid, thallium salt (8, 9) (41830-88-0) Benzoic acid, thallium (1+) salt (8,9) (5630-31-9) Succinimide, N-iodo- (8) 2,5-Pyrrolidinedione, 1-iodo- (9) (516-12-1)... 

Bielawska and Michalska [511] have introduced S-(2-deoxyglycosyl)phosphor-othioates as glycosyl donors. Activation of these compounds for glycosidation with silver salts (AgF, AgC104 or AgOTf) resulted in the formation of 2 -deoxydisacchar-ides as anomeric mixtures. Thiem and coworkers reported [507] an efficient activation method for S-(2-deoxyglycosyl)phosphorothioate donors 102 by using N-iodo-succinimide (NIS) or iodonium bis(2,4,6-trimethylpyridine) perchlorate (IDCP) (Scheme 4.94). 

The notorious propensity for terminal olefins to undergo non-selective epoxidation has been overcome in one case by the stepwise formation of the epoxide. Thus, a Merck group capitalized on the chiral environment of oxazolidine 40 by first carrying out a diastereoselective iodohydration using N-iodo succinimide (NIS) under a carefully chosen set... 

Recently, several more effective activators have been introduced, including NBS [35], methyl triflate [38], dimethyl(methylthio)sulfomum triflate (DMTST) [39], N-iodo-succinimide-triflic acid (NiS-TfOH) [40], and trimethylsilyl triflate (TMSOTO (41]- The... 

N-Iodoamides and y-lactones. Barton and co-workers found i-butyl hypoiodite to be an excellent reagent for the preparation of N-iodo derivatives of amides (benz-amide, succinimide, n-butyramide, ocladecaneamide). An N-iodoamide of suitable structure (2) is converted on photolysis Into the y-lactone (3). 

AUylic bromination. [1, 79. after citation of ref. 8]. N-Bromosuccinimide reacts with isolapachol (I) in refluxing CCT by vinylic substitution to give (2) N-iodo-succinimide reacts in the same way.83 (8-1 sopropylfurano- 1,4-naphthoquinone (3) was obtained by cyclization of the vinylic bromide (2) with N1S and also by the action of two equivalents of N IS on (1). Even when the unsaturated side chain has a primary or secondary hydrogen in the allylic position, for example (4), the same vinylic substitution was observed (5). 

KOBr-soln. prepared from Brg and KOH in water added dropwise at room temp, to an agitated slurry of 8-quinolinol-5-sulfonic acid in aq. KOH, and stirring continued 1 hr. 7-bromo-8-quinolinol-5-sulfonic acid. Y 95%. Cl-Analog with NaOCl, and 7-iodo-8-quinolinol from bis-(8-quinolinolato)copper(II) with N-iodo-succinimide, s. H. Gershon, M.W. McNeil, and A. T. Grefig, J. Org. Chem. 34, 3268 (1969). 

N-Bromo- [104-106] or N-iodo- [107] succinimide are efficient reagents for the oxidation of aldehydes to carboxylic acid derivatives. The corresponding acyl halides are formed as intermediates, which are easily converted into acids [104], esters [105,... 

The conversion of 3-deoxy-3-hydrazino-l,2 5,6-di-0-isopropylidene-n-allofuranose into the corresponding 3-deoxy-3-halo-D-glucose derivative by A-iodo-, A-bromo-, or A-chloro-succinimide may proceed by way of a diazonium intermediate formed by initial oxidation of the hydrazino derivative. The reaction is, however, probably more complex, as the oxidation by iodine in aqueous potassium iodide gave the gem di-iodo derivative. ... 

The reductive cyclization of N-(w-iodoalkyl)succinimides induced by samarium(II) iodide was disclosed by Ha et al. as a novel method for making pyrrolizidines and indoUzidines (Scheme 46). " In the apphcation of the method to the synthesis of (+)-lentiginosine (127), reaction of N-(4-iodo-butyl)tartarimide (+)-335 with samarium(II) iodide in the presence of the iron(III)—tris(dibenzoylmethane) complex as catalyst produced the unsaturated indolizidin-3-one (+)-336 in 82% yield. Reduction of the bridgehead alkene was accomplished with triethylsilane and trifluoroacetic acid via an intermediate acyliminium ion, giving (+)-337 as the sole product in 93% yield. Routine hydrolysis of the silyl ethers produced the known diol (+)-177, after which reduction of the lactam with Hthium aluminum hydride then completed this short synthesis of (+)-127. 

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