Synthesis of Alkynylthiopyridinium Salts and Their Use as Thioketene Equivalents

Autor:	Henner Pesch, Kai F. G. Averesch, Manuel Alcarazo, Christopher Golz
Rok vydání:	2019
Předmět:	Steric effects 010405 organic chemistry Organic Chemistry General Chemistry 010402 general chemistry 01 natural sciences Thioketene Catalysis 0104 chemical sciences chemistry.chemical_compound Nucleophile chemistry Organic chemistry Reactivity (chemistry) Pyridinium
Zdroj:	Chemistry – A European Journal. 25:10472-10477
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201901895
Popis:	A synthetic method has been developed for the preparation of dihalo(pyridinium)sulfuranes and their transformation into alkynylthiopyridinium salts, starting from inexpensive thiopyridones. The reactivity of these salts towards different nucleophiles is evaluated. Most thiols and amines are converted into dithioesters and thioamides, respectively; whereas sterically demanding thiols delivered alkynylthioethers. These results, together with preliminary mechanistic studies reveal that alkynylthiopyridinium salts can be considered synthetic equivalents of unstable thioketenes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b66ff13c57dc252dc4e0d8e5700cbf8e https://doi.org/10.1002/chem.201901895 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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