IV- succinimide

Numerous derivatives of imidazoline nitroxides with various functional groups have been obtained in the investigations of reactions of 4-alkyl-halide- and 4-alkyl-dihalide-3-imidazoline-3-oxides. The interaction of compounds 7a,b with an equimolar quantity of iV-bromo- and N-chloro-succinimide leads to 4-bromomethyl-, 4-a-bromoethyl-, and 4-a-chloro-ethyl-3-imidazoline-3 oxides (64a,b) (Kutikova and Volodarsky, 1973 Grigor ev and Volodarsky, 1975). With the addition of excess iV-succinimide halide 4-dibromomethyl-, 4-dichloromethyl-, and 4-a,a-dichloroethyl-3-imidazoline-3-oxides (65a,b) are formed (Grigor ev and Volodarsky, 1974 Grigor ev et a/., 1975 Mitasov et ai, 1978). Nitroxides 64 and 65 are reduced by zinc to diamagnetic 1-hydroxy-derivatives 66 and 67. 

Methyl y-bromocrotonate. Mix 36 g. of iV-bromosuccinimide, 40 g. of methyl crotonate and 60 ml. of dry, redistilled carbon tetrachloride in a 500 ml. round bottomed flask. Reflux ou a water bath for 12 hours by this time all the sohd should have risen to the surface of the liquid. Filter off the succinimide at the pump and wash it with a little dry carbon tetrachloride. Remove the solvent on a water bath and distil the residue under reduced pressure, preferably from a Widmer flask (compare Figs. II, 24, 4-5). Collect the methyl y-bromocrotonate at 77-78°/8 mm. the yield is 31 g. 

The earliest oxidations were effected with nitrous fumes and later with mercuric oxide and isoamyl nitrite.74 Lead tetraacetate in acetic acid is in many cases the reagent of choice, but the removal of by-products can present some difficulties.75 IV-Haloimides and amides in alcoholic solutions have been reported to yield essentially pure tetrazolium salts76 and have been found specially useful in the preparation of heteroaryl-substituted tetrazolium salt.77,78 The novel formazans 49 have been successfully oxidized to 50 using 7V-chloro succinimide (Eq. II).79 tert-Butyl hypo-... 

Analogously, when the reaction of iV-(phenylseleno)phthalimide or TV-(phenylseleno) succinimide with 3 is carried out in methylene chloride in the presence of 2-3 equivalents of water, compound 175 can be obtained in high yield (equation 141)16. A mixture of isomeric cyclic ethers 175 and 176 was obtained also by treatment of 3 with phenylse-lenocyanide, in the presence of copper(II) chloride (equation 142)143. 

The Beckmann rearrangement of ketoximes with triphenylphosphine and iV-chloro-succinimide occurs at room temperature almost instantaneously and their corresponding secondary amides are obtained in high yields (equation 83). The triphenylphosphine 271 is activated by the iV-chlorosuccinimide 270 affording the salt 272, which is attacked by the iV-hydroxy group of the oxime 217 forming the intermediate 273. 

Bugge brominated thienothiophenes 1 and 2 with IV-bromo-succinimide in glacial acetic acid to 2-bromothieno[2,3-6]thiophene (66%) and 2-bromothieno[3,2-6]thiophene (55%). The structure of 2-bromothieno[2,3-6]thiophene was confirmed by the replacement of bromine by lithium at —70° followed by carbonation to thieno[2,3-6j-thiophene-2-carboxylic acid 2-bromothieno[3,2-fe]thiophene was independently prepared by the treatment of 2-lithiothieno[3,2-6]thiophene with one equivient of bromine at —70°. The 2-bromo derivatives of thienothiophenes 1 and 2 decompose within several hours at 20°, but remain uncWged for weeks at —15°. 

Slepnev et al. [313] presented a simple method for protein radio-labeling with Bolten-Hunter reagent (iV-hydroxy succinimide ester of 3-(p-hydroxy di-iodophenyl)) propionic acid) in AOT/octane-RMs using mouse IgG, human transferrin, protein A, and a2-interferon as labeling examples. The yield of radio-labeling in RMs was found to be higher than that achieved in homogeneous aqueous solution. 

METHYL y-BROMOCROTONATE IV-Bromosuccinimide. Dissolve, with the aid of rapid mechanical stirring, 80 g. of pure succinimide (Section V,14) in a mixture of 150 g. of finely crushed ice and a solution of 32 g. of sodium hydroxide in 200 ml. of water contained in a litre beaker and cooled externally by ice. Immediately the imide has dissolved, continue the vigorous stirring and introduce 42 -5 ml. of bromine in one lot from a separatory funnel supported over the beaker it is essential that the bromine be instantly suspended in the solution. After stirring vigorously for 2 minutes, filter at the pump and... 

Incorporation of the pyrrolidine-2,5-dione (succinimide) ring system into a polymeric framework has been accomplished in a variety of ways. The first method involves the addition polymerization of a suitably substituted derivative of succinimide. Several vinyl derivatives, including l-vinylpyrrolidine-2,5-dione (IV-vinylsuccinimide), have been described (B-74MI11100). Several groups have carried out investigations on polymerizable derivatives of A-hydroxysuccinimide, some examples of which are shown in Scheme 2... 

Tetrahydrobenzo[6]thiophene103 and several benzo[6]thio-phenes containing electron-donating substituents, e.g., 5,6-dimeth-oxy,180 5,6-methylenedioxy,180 6-ethoxy,424 3-methoxy,183 and 3-methyl,487 are smoothly brominated in the 2-position by iV-bromo-succinimide in carbon tetrachloride or chloroform in the absence of peroxides. Similar treatment of 2-methoxybenzo[6]thiophene gives the 3-bromo derivative.183... 

Succinimide and DMAD give a Michael 1 1 adduct,113 but iV-bromo-succinimide with acetylenic esters in acetic acid led to electrophilic addition of bromine to the triple bond.114... 

In a 500-ml round-bottomed flask place 39.4 g (0.20 mol) of iV-bromo-succinimide (Section 4.2.10, p. 422), 49.2 g (0.60 mol) of redistilled cyclo-hexene, 150 ml of carbon tetrachloride and about 500 mg of benzoyl peroxide (CAUTION Section 4.2.6, p. 417), previously dried by pressing between filter papers. Attach a double surface reflux condenser and allow the mixture to stand at room temperature when after a short induction period the reaction begins. The reaction mixture becomes warm and the heavy yellowish N-bromosuccinimide begins to be transformed into the light colourless succinimide which becomes suspended in the reaction mixture. When the reaction has moderated somewhat, transfer the flask to a steam bath and heat under reflux until all the iV-bromosuccinimide has been converted to succinimide (about 1.5 hours) (1). Cool the flask, filter under suction and wash the residue... 

Succinimide-iV-sulphenyl chloride. Chlorine gas (CAUTION) is passed for 8 hours through a stirred solution of the foregoing compound (53.7 g) in chloroform (250 ml) warmed to 50 °C. Nitrogen gas is passed through the mixture to remove excess chlorine, followed by evaporation in vacuo to give succinimide-N-sulphenyl chloride (65.1 g, 93.3%) as yellow crystals, m.p. 65-67 °C. 

Ring-expansion substitution reactions of 1,3-dithiolanes and 1,3-dithianes with N-halo- and IV-cyano-succinimide give mono-halo- and -cyano-l,4-dithiins and -1,4-dithiepins (Scheme 19). With NBS and BU4NN3 and NBS and NH4SCN, the azido and thiocyanato analogues are formed, respectively.35... 

Carboxylic acid iV-hydroxy-succinimide ester iV-Methyl-nicotinic acid iV-hydroxysuccinimide ester [21] Phenolic OH LC-ESP/MS/ MS... 

Dehydrogenation of tetrahydrothiopyran-4-ones to the 5,6-dihydro derivative has been achieved with iV-chloro-succinimide <1992HCA1925>. A similar approach converts dihydroisothiocoumarins to the isothiocoumarins, with initial bromination by NBS at the 4-position being followed by dehydrobromination using triethylamine (Scheme 99) <2000T6763>. 

N-Bromosuccinimide and IV,IV-dibromo-5,5-dimethylhydantoin have also been used successfully, which makes possible recycling of succinimide or the hydantoin and utilizes all the bromine atoms. A mixture of sodium bromide—sodium bromate in aqueous acid has also been used commercially. 

The photoelectron spectrum of pyrrolidine in the low-energy (8-13 eV) region has been explored as part of a study of lone-pair ionization processes and an IP of 8.82 eV recorded for ionization from the N lone-pair. In iV-methyl-3-pyrrolidinone the bands at 8.83, 9.53 and 12.24 eV have been assigned to ionization from the N lone-pair, the O lone-pair and the carbonyl 7r-system respectively. In 2-pyrrolidinone the first two bands are overlapped (at 9.53 and 9.76 eV), presumably a result of the amide resonance interaction, and on the basis of band appearance a reversed assignment to O lone-pair and N lone-pair ionization respectively has been proposed the ttco ionization band is at 11.91 eV. Data are also available in the same paper for succinimide and its Af-chloro and Af-bromo derivatives (78MI30407). 

Reagents i, NaBH4 ii, PI1CH2OCOCI iii, Killiani oxidation iv, (CH2SH)2 v, Raney Ni vi, JV-chloro-succinimide vii, NaOMe viii, MnOz ix, silica gel... 

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