Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives

Article abstract of DOI:10.1016/S0008-6215(97)00044-X

Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds.