β Scribed by Youlia Hagooly; Michael J. Welch; Shlomo Rozen
No coin nor oath required. For personal study only.
Synthesis of Difluoroaryldioxoles Using BrF 3 . -Treatment of catechols with thiophosgene provide the corresponding thiodioxoles which upon treatment with bromine trifluoride produce potentially biologically important difluoroaryldioxoles in good to very good yields. Compounds which are activated or mildly deactivated towards electrophilic attack are ring brominated, in addition to formation of the difluorodiether moiety, cf. (VII) and (VIII). In the case of intermediate (VIc), the protecting group is cleaved to afford the novel benzodioxole derivative (IX). An involvement of a radical pathway, producing a stable benzyl radical, is supposed. The reaction is also applicable to heteroaromatics such as pyridine derivatives (X). -(HAGOOLY, Y.; WELCH, M.
π SIMILAR VOLUMES
## Abstract A range of aromatic (V) and aliphatic CF~3~βcontaining derivatives, e.g. (XI), is prepared by conversion of the corresponding carboxylic acids into dithioesters and subsequent SβF exchange reaction with bromine trifluoride under mild conditions.