A-Chlorosuccinimide

Similar halogenations have been done on 2-lithio-l-phenylsulfonylindole[2], 2-Lithio-l-phenylsulfonylindole is readily converted to the 2-(trimethylsilyl) derivative[2,3]. 2-Trialkylstannylindoles can also be prepared via 2-lithio-indoles[4,5], 2-Sulfonamido groups can be introduced by reaction of a 2-lithioindole with sulfur dioxide, followed by conversion of the sulfinic acid group to the sulfonyl chloride with A-chlorosuccinimide[6]. 

A -Chlorosuccinimide [128-09-6] M 133.5, m 149-150 . Rapidly crystd from benzene, or glacial acetic acid and washed well with water then dried in vacuo. [Phillips and Cohen J Am Chem Soc 108 2023 1986.]... 

A solution of hydrazoic acid (prepared from about 30 g sodium azide) in ca. 200 ml chloroform is prepared in a well-ventilated hood. Cholesterol (15 g) is dissolved in the hydrazoic acid solution and 3.5 ml of triethylamine is added. The reaction mixture is then stirred at room temperature while 7 g of A-chlorosuccinimide is added. The reaction mixture is allowed to stand overnight and then the chloroform solution is washed successively with dilute sodium bisulfite, dilute soldium bicarbonate solutions and finally with water. The chloroform extract is then dried (Na2S04) and the solvent removed in vacuo. The residue is crystallized from ethanol to yield ca. 8.5 g of (101) in colorless needles mp 138-139°. The chloro azide is reduced to the aziridine by lithium aluminum hydride according to the foregoing procedure. 

A-Chlorosuccinimide 1 N NaOH." With this method, the sulfide is oxidized completely to the sulfone, which is cleaved with hydroxide more readily than the sulfoxide formed by periodate oxidation. It has been reported that oxidation of the sulfide leads to oxidation of adenine and gua-nine." However, see the discussion of the TPTE group below. 

NCS (A -chlorosuccinimide), and A -fluoropyridinium triflate (90JA8563), [or A-fluorodibenzenesulfonimide (91SL187)], respectively. 

The required A-chloroamines 9 can be prepared from the corresponding amine by treatment with sodium hypochlorite or A-chlorosuccinimide. 

Another decarboxylation reaction that employs lead tetraacetate under milder conditions, has been introduced by Grob et alJ In that case A-chlorosuccinimide is used as chlorinating agent and a mixture of A,A-dimethylformamide and acetic acid as solvent. 

Controlled chlorination with A-chlorosuccinimide results in the formation of square pyramidal RhHCl2(PPr3)2 and planar RhCl2(PPr 3)2 (Figure 2.65). 

Norbomadiene A-Bromosuccinimide A-Chlorosuccinimide A-Iodosuccinimide Raney nickel... 

A. Chlorinating agents Sodium hypochlorite solution A-Chlorosuccinimide Chloramine-Tb... 

Furyllithium reacts rapidly with trialkylborons though the furylborons 91 believed to be formed are not actually isolated. Treated with an electrophile (iodine or A-chlorosuccinimide), they transfer one alkyl residue to the furan ring and eject the boron residue in a reaction well known in other series (Scheme 46). The 2-alkylfurans are indeed produced in excellent yields and the method is better than many other syntheses.236... 

The reaction of nitrones of the 3-imidazoline series (295) with bromine and amyl nitrite, in the presence of base, gives a-tribromomethyl-(296) and a-hydroxyaminomethyl derivatives (297) (538). Bromination of nitrones (295) with N -bromosuccinimide (NBS) in CCI4 or bromine in methanol leads to the formation of a-bromoalkyl (298 a,b, Hal = Br) and a-dibromomethyl (299) nitrones (539-541). The reaction with iodine in methanol gives the mono iodo derivative (300) (541). The reaction with A-chlorosuccinimide (NCS) in CCI4 leads to a-chloroethyl nitrones (298b, Hal = Cl) and a,a-dichloromethyl nitrones (301) (Scheme 2.118) (225). 

GABA HMG-CoA HMPA HT LDA LHMDS LTMP NADH NBH NBS NCS NIS NK NMP PMB PPA RaNi Red-Al RNA SEM SnAt TBAF TBDMS TBS Tf TFA TFP THF TIPS TMEDA TMG TMP TMS Tol-BINAP TTF y-aminobutyric acid hydroxymethylglutaryl coenzyme A hexamethylphosphoric triamide hydroxytryptamine (serotonin) lithium diisopropylamide lithium hexamethyldisilazane lithium 2,2,6,6-tetramethylpiperidine reduced nicotinamide adenine dinucleotide l,3-dibromo-5,5-dimethylhydantoin A-bromosuccinimide A-chlorosuccinimide A-iodosuccinimide neurokinin 1 -methyl-2-pyrrolidinone para-methoxybenzyl polyphosphoric acid Raney Nickel sodium bis(2-methoxyethoxy)aluminum hydride ribonucleic acid 2-(trimethylsilyl)ethoxymethyl nucleophilic substitution on an aromatic ring tetrabutylammonium fluoride tert-butyldimcthyisilyl fert-butyldimethylsilyl trifluoromethanesulfonyl (triflyl) trifluoroacetic acid tri-o-furylphosphine tetrahydrofuran triisopropylsilyl A, N,N ,N -tetramethy lethylenediamine tetramethyl guanidine tetramethylpiperidine trimethylsilyl 2,2 -bis(di-p-tolylphosphino)-l,r-binaphthyl tetrathiafulvalene... 

All primary amines react with fluorescamine under alkaline conditions (pH 9-11) to form a fluorescent product (Figure 10.12) (excitation maximum, 390 nm emission maximum, 475 nm). The fluorescence is unstable in aqueous solution and the reagent must be prepared in acetone. The secondary amines, proline and hydroxyproline, do not react unless they are first converted to primary amines, which can be done using A-chlorosuccinimide. Although the reagent is of interest because of its fast reaction rate with amino acids at room temperature, it does not offer any greater sensitivity than the ninhydrin reaction. 

Many of the reactions of A-chloro- and A-bromo-imides are extremely violent or explosive. Those observed include A-chlorosuccinimide with aliphatic alcohols or benzylamine or hydrazine hydrate A-bromosuccimmidc with aniline, diallyl sulfide, or hydrazine hydrate or 3-nitro-A-bromophthalimide with tetrahydrofur-furyl alcohol l,3-dichloro-5,5-dimethyl-2,4-imidazolidindione with xylene (violent explosion). Individually indexed compounds are ... 

This latter compound, 36, and the isomeric 9-oxabicyclo[4.2.1]nonane, 37, were obtained as the sole products, in ca 13 87 ratio, by reaction of 3 with A-chlorosuccinimide (NCS) in protic solvents (methanol, dioxane-water mixtures)72. It is noteworthy that similar ratios of the two disubstituted bicyclononane derivatives were obtained, independently of the solvent, also by using A-bromosuccinimide (NBS) as electrophile, whereas a strongly solvent-dependent ratio was observed when A-iodosuccinimide (NIS) was used. Since these reactions should proceed through hydroxy- or alkoxyhalogenation of one of the double bonds, followed by transannular attack of the oxygen function on the cationic center which is formed on the other side of the ring by the reaction of another electrophile with the second double bond, the isomer ratio has been rationalized in terms of a different nature of the intermediates. 

A -chlorosuccinimide yields dichloro-substituted [N(PPh3)2][7,l l-Cl2-2,2,2-(CO)3-c/o50-2,l-FeCBioH9] (42). In each of these products, hydride replacement again occurs at boron atoms that are p with respect to the carbon atom in the iron-bound CBBBB face, a feature confirmed by an X-ray diffraction study upon complex 42. This site of substitution was also verified by treatment of 41 with Ag[Bp4] in the presence of THF, which afforded compound 30 via Agl elimination. 

Sodium periodate or positive halogenanting species such as A-chlorosuccinimide and f-bntyl hypochlorite" are nsefnl oxidizing reagents. 

A -Chlorosuccinimide, 1427 N -Chlorotetramethylguanidine, 2004 Diamminedichloroamidotrichloroplatinum(IV), 4179 2,6-Dibromobenzoquinone-4-chloroimide, 2076 Dichloramine, 4063 A, A -Dichloro-jd-alanine, 1168... 

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