Formation of sulfur-centered cation radicals by photofragmentation

Laser flash photolysis of sulfonium peresters afforded two-sulfur, three-electron stabilized cation radicals. The selected dialkyl dithioethers 1,5-dithiocane, 1,4-dithiepane, 1,4-dithiane, and 2,6-dithiaheptane are readily monoalkylated in nitromethane by tert-butyl O-trifluoromethanesulfonyl-3-hyd...

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Veröffentlicht in:	Tetrahedron letters 1992-03, Vol.33 (13), p.1721-1724
Hauptverfasser:	Glass, Richard S., Broeker, Jeffrey L., Anklam, Elke, Asmus, Klaus-Dieter
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology General and physical chemistry laser flash photolysis perester fragmentation Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Sulfur-centered cation radical formation
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Zusammenfassung:	Laser flash photolysis of sulfonium peresters afforded two-sulfur, three-electron stabilized cation radicals. The selected dialkyl dithioethers 1,5-dithiocane, 1,4-dithiepane, 1,4-dithiane, and 2,6-dithiaheptane are readily monoalkylated in nitromethane by tert-butyl O-trifluoromethanesulfonyl-3-hydroxyperoxypropanoate, 6, to give the corresponding sulfonium salt peresters 2a-c, and 3 in good yield. Laser flash photolysis of these compounds affords the known two-sulfur, three-electron stabilized cation radicals 2a, b, and 5 which were characterized by optical absorption spectroscopy.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/S0040-4039(00)91715-5