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- W2766712262 abstract "Abstract Herein the addition of different thiols to the strained carbon–carbon bond of [1.1.1]propellane ( 1 ) is reported. The reaction pathway was investigated, addition reactions with substituted thiols, hydrogen sulfide and protected cysteine were performed, and further modifications of the products were verified. The clean reaction proceeds by a radical chain process, which was confirmed by different deuterium labelling experiments. It shows high functional‐group tolerance, since halo‐, hydroxy‐, methoxy‐, carboxy‐, amino‐ and nitro‐substituted thiols could be added to 1 with few by‐products in 16–90 % yield. Oxidation of the products allows tuning of the polarity and subsequent reactions of the products. The click‐type reaction proceeds even faster with selenols, as was shown in a proof of concept. Thiol addition to 1 offers a facile tool for surface modification, conjugation and tuning of hydrophilicity in bio‐ and medicinal chemistry." @default.
- W2766712262 created "2017-11-10" @default.
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- W2766712262 date "2017-12-18" @default.
- W2766712262 modified "2023-10-14" @default.
- W2766712262 title "Alkyl and Aryl Thiol Addition to [1.1.1]Propellane: Scope and Limitations of a Fast Conjugation Reaction" @default.
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- W2766712262 doi "https://doi.org/10.1002/chem.201704105" @default.
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