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Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processes accessible, acetyl-protected thiols

Alfred Blaszczyk, Mark Elbing and Marcel Mayor*

*Institute for Nanotechnology, Forschungszentrum Karlsruhe GmbH, P. O. Box 3640, D - 76021, Karlsruhe, Germany, Email:

A. Blaszczyk, M. Elbing, M. Mayor, Org. Biomol. Chem., 2004, 2, 2722-2724.

DOI: 10.1039/b408677e (free Supporting Information)


The facile and efficient conversion of a tert-butyl protecting group to an acetyl protecting group for thiols by catalytic amounts of bromine in acetyl chloride and the presence of acetic acid has been developed. The fairly mild reaction conditions are of particular interest for new protecting group strategies for sulfur functionalised target structures.

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Key Words

Thiols, Protecting Groups, Esters, Thioesters

ID: J52-Y2004-730