Phase-transfer-catalyzed reactions between polysulfide anions and .alpha.,.beta.-unsaturated carbonyl compounds

Autor:	Eitan B. Krein, Zeev Aizenshtat
Rok vydání:	1993
Předmět:	chemistry.chemical_compound Bicyclic molecule Dibenzylideneacetone Chemistry Dimer Sodium polysulfide Organic Chemistry Polymer chemistry Benzylideneacetone Ring (chemistry) Polysulfide Catalysis
Zdroj:	The Journal of Organic Chemistry. 58:6103-6108
ISSN:	1520-6904 0022-3263
Popis:	Ammonium polysulfide reacts with α,β-unsaturated ketones and aldehydes under PTC (phase transfer catalysis) conditions in a rather different manner than it does in homogeneous systems. 1,3-Diphenyl-2-propen-1-one (chalcone, 1) and 4-phenyl-3-buten-2-one (benzylideneacetone, 3) give sulfur-linked dimers (mainly disulfides). 3-Phenyl-2-propen-1-al (cinnamaldehyde) polymerizes. 1,5-Diphenyl-1,4-pentadien-3-one (dibenzylideneacetone, 7) gives the known six-membered ring thianones and new seven-membered ring 1,2-dithiepanones 9 along with a polymer. Carvone gives a disulfide dimer that converts to a mixture of bicyclic sulfur-containing compounds. Sodium polysulfide is much less effective because of the base-induced decomposition of either the products or the intermediates
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f9c1fba7630df005a41ff1c742e6a703 https://doi.org/10.1021/jo00074a043 Zobrazit plný text záznamu