Alkylating agents powerful

FS(0)20CH3. Colourless liquid, b.p. 94°C. Functions as a powerful methylating agent, even for amides and nitriles which are not attacked by conventional alkylating agents like dialkyl sulphates. 

The fact that the isomeric structure of azolides is thermodynamically controlled has been used by Olofson and Kendall to prepare 1-alkylazoles regioselectively (70JOC2246). An asymmetric pyrazole yields two alkylated derivatives (Scheme 21 see Section 4.04.2.1.3 (viii)), but the alkylation with a powerful alkylating agent of the acetylated derivative leads to the less abundant isomer via the salt (249), which is too unstable to be isolated. 

Ethyl trifluoromethanesulfonate [425-75-2] M 178.1, b 115 /atm, 118-120 /atm, d 1.378, Hp 1.336. The ester reacts slowly with H2O and aqueous alkali. If its IR has no OH bands (-3000 cm" ) then purify by redistillation. If OH bands are present then dilute with dry Et20 and shake (carefully) with aqueous NaHC03 until effervescence ceases, then wash with H2O and dry (MgSOa), filter, evaporate and distil the residue under slight vacuum then at atmospheric pressure in a N2 atmosphere. IT IS A POWERFUL ALKYLATING AGENT, AND THE FUMES ARE VERY TOXIC - CARRY ALL OPERATIONS IN AN EFFICIENT FUME CUPBOARD. [Gramstad and Hazeldine J Chem Soc 173 7956 Howells and McCown Chem Rev 77 69 1977.]... 

Meerwein s reagent, triethvloxonium tetrafluoroborate, is a powerful ethylating agent that converts alcohols into ethyl ethers at neutral pH. Show the reaction of Meerwein s Teagent with cyclohexanol, and account for the fact that trialkyloxonium salts are much more reactive alkylating agents than alkyl iodides. 

Method H (with microwave irradiation) An intimate mixture of the methylenesulphone (5 mmol), alkylating agent (5 mmol), TEBA-I (0.23 g, 1 mmol) and anhydrous K2C03 (3 g, 22 mmol) is irradiated on low power using a 960 W microwave oven for 2-3 min. The product is isolated using the procedure described in 6.2.13.A,... 

Alkali tellurides, among which sodium telluride is the most widely employed, are powerful nucleophilic reagents and therefore react easily with alkylating agents. 

Besides being used as an alkylating agent in cancer chemotherapy, cyclophosphamide is a unique drug when used as an immunosuppressant. First, it is the most powerful of all such drugs. Second, it kills proliferating cells, and evidently alkylates a certain region of... 

Elsewhere the author has published examples of the use of hydrogen fluoride to catalyze the alkylation of benzene using a variety of alkylating agents (Simons, 22, 23, 24). The breadth and scope of the catalytic power of hydrogen fluoride can be better obtained by a more complete examination of the alkylations now published using this catalyst. For reasons of organization, the subject is divided into aromatic and aliphatic reactions. 

The Jackson laboratory of the du Pont Company soon became interested in the catalytic power of hydrogen fluoride. The results of its work are recorded in three excellent papers. Using acrolein as the alkylating agent and hydrogen fluoride as the catalyst, peri syntheses have been performed (Calcott et al, 32), both those that are catalyzed by sulfuric acid and others that are not. By appropriate condensation, dehydration, and reduction, perylene was obtained from phenanthrene... 

The trialkyloxonium salts are powerful alkylating agents. Trimethyl- and triethyloxonium tetrafluoroborates, in particular, have been widely employed for methylation and ethylation of sensitive or weakly nucleophilic functional groups. Alkylations of over 50 such functional groups have been reported in the literature. Examples include amides,4,7,13 16 lac-... 

DNA injury can initiate apoptosis by a powerful, early activated mechanism mediated by the nuclear phosphoprotein p53. This protein is activated by both transcriptional and posttranslational means and is critical in the cellular response to double-strand DNA breaks, which can be induced by high-energy radiation such as UV light. Although the detailed mechanisms are not well understood, p53 apparently plays a regulatory role whereby the cell is directed either toward the completion of repair or to apoptosis (W20). In fact, p53 was proven to be essential for the induction of apoptosis of some cells treated with DNA alkylating agent (W19). 

The sulfur atom of thiophenes is weakly nucleophilic and can act in some cases as the site for attack of an electrophilic reagent. In strongly acidic solutions the a-carbon atom is protonated (66RTC1072) this could be a thermodynamically controlled product, however. Reaction of thiophene with powerful alkylating agents provides the thiophenium salt (56),... 

However, a-chloroketones are powerful alkylating agents and the bound inhibitor attacks His 57 of the catalytic triad system. The reaction is probably more complex than is indicated in the foregoing equation and may involve an epoxy ether intermediate/ Many other peptide chloromethyl ketone inhibitors have been devised/ 1 ... 

In principle, conversion of a primary or secondary amine into its conjugate base, RNH or R2N , should make the nitrogen powerfully nucleophilic toward alkylating agents ... 

Many efforts have been directed to the regioselective substitution of either HO-2 or -3 and to stereocontrolled addition reactions to the double bond. The acylation and alkylation of such hydroxyl groups is fairly sensitive to the reaction conditions. It is reported that alkylation of ascorbic acid in solvents of high dielectric constant favors 2-C-alkylation when powerful alkylation agents were employed.346... 

Methyl triflate is a powerful alkylating agent, which methylates tetracovalent P=0, P=S, and P=Se systems at the oxygen, sulfur, and selenium atoms, respectively (1,2, 3). Its reaction with analogs containing a hydrogen substituent (e .j>., phosphinate, phosphonate or secondary phosphine oxide species), however, appears not to have been reported. 

In summary, DMH and AOM failed to increase in vitro mutagenic frequency with or without liver extracts. However, MAM caused a dose-dependent increase in reversion frequency without hepatic enzymes as expected since MAM decomposes heterolytically to methyl-diazonium and formaldehyde (32). Methyldiazonium ions yield nitrogen and methylcarbonium, a powerful alkylating agent. Formaldehyde is oxidized to (X. In contrast to in vitro conditions, the host-mediated assay showed that intact animals converted DMH and AOM to mutagenic products. 

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