Alkylation polyfunctional alkylating agents

Haloall lation. Haloalkyl groups can be introduced directiy by processes similar to Friedel-Crafts alkylation into aromatic and, to some extent, ahphatic compounds. Because halo alkylations involve bi- or polyfunctional alkylating agents, they must be performed under conditions that promote the initial halo alkylation but not, to any substantial degree, subsequent further alkylations with the initially formed haloalkylated products. 

Murphy, M.L., Del Moro, A., Lacon, C. (1958). The comparative effects of five polyfunctional alkylating agents on the rat fetus, with additional notes on the chick embryo. Ann. NY Acad. Sci. 68 762-82. 

Murphy, L. M. A comparison of the teratogenic effects of fine polyfunctional alkylating agents on the rat fetus. Pediat., 1959, 231-244. 

I 10. The answer is a. (Hardman, p 1302.) Cyclophosphamide is classified as a polyfunctional alkylating drug that transfers its alkyl groups to cellular components. The cytotoxic effect of this agent is directly associated with the alkylation of components of DNA. Methotrexate and 5-FU are classified as antimetabolites that block intermediary metabolism to inhibit cell proliferation. Tamoxifen is an antiestrogen compound. Doxorubicin is classified as an antibiotic chemotherapeutic agent. 

In this chapter, only special examples of stoichiometric acylation will be commented. For example, reactions showing extraordinary level of regiose-lectivity promoted by proximity or metal template effects are described. Moreover, examples of efficient use of carboxylic acids and esters as acylating agents under soft experimental conditions in combination with ecocompatible solvents are stressed as new and practicable synthetic methods. Studies on the highly efficient multistep s)mthesis of polyfunctional compounds via bis-acylation and alkylation-acylation processes are commented upon, and some mechanistic details are also shown. 

EP 56-526 1982 Mobil Oil Corp. Radiation cdrable coating composition comprising an acrylic ester monomer and polyfunctional acrylate crosslinking agents. The use of the adduct of (meth) acrylic acid or its hydroxy-alkyl ester and bisphenol A diglycidyl ether is claimed. 

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