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Adolfo Lopez Torres; Eunice Yanez Barrientos; Katarzyna Wrobel; Kazimierz Wrobel. Selective derivatization of cytosine and methylcytosine moieties with 2-bromoacetophenone for submicrogram DNA methylation analysis by reversed phase HPLC with spectrofluorimetric detection. Analytical chemistry 2011, 83 (20), 7999-8005.

Reagent for carboxyl protection as phenacyl esters, stable to acid hydrolysis but readily cleaved by nucleophiles or by reduction. See Appendix 6. Protection can be effected in the presence of triethylamine: J. Chem. Soc. (C), 1191 (1966), or, better, KF in DMF: Tetrahedron Lett., 599 (1977). Phase-transfer conditions have also been reported: Synth. Commun., 26, 1747 (1996). Cleavage has been described using a variety of reagents, including Zn-AcOH: Tetrahedron Lett., 343 (1970), catalytic hydrogenolysis, treatment with PhS-, PhSeH, or NaHTe: Synth. Commun., 18, 116 (1988); TBAF: J. Org. Chem., 56, 5465 (1991); or photolysis: J. Org. Chem., 62, 6245 (1997).

Has also been used to block the imidazole ring in histidine residues during peptide synthesis, and is stable to TFA, TfOH and HBr-AcOH: J. Chem. Soc., Chem. Commun., 472 (1978); J. Chem. Soc., Perkin 1, 2261 (1979).

For formation of the Sn enolate using SnCl2, see: Synth. Commun., 23, 271 (1993). 1,4-Diketones may be synthesized from -bromoketones and Sn enolates: J. Chem. Soc., Perkin 1, 3205 (1990).