PUMMERER REARRANGEMENT PROMOTED BY POLYPHOSPHORIC ACID TRIMETHYLSILYL ESTER (PPSE)
نویسندگان
چکیده
منابع مشابه
Pummerer fragmentation vs. pummerer rearrangement: a mechanistic analysis.
Depending upon the nature of the substituent at the beta-position of the sulfoxide moiety, a Pummerer reaction can be oriented "at will" towards Calpha-H (rearrangement) or Calpha-Cbeta (fragmentation) bond cleavage.
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The first general procedure for the synthesis of 5 to 7-membered 1-aryl-2-iminoazacycloalkanes is presented, by microwave-assisted ring closure of ω-arylaminonitriles promoted by polyphosphoric acid (PPA) esters. 1-Aryl-2-iminopyrrolidines were easily prepared from the acyclic precursors employing a chloroformic solution of ethyl polyphosphate (PPE). The use of trimethylsilyl polyphosphate (PPS...
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[2.2]Paracyclophanes, incorporating functional groups in the aliphatic bridges, suitable for elimination to give [2.2]paracyclophanedienes, are synthesized through a novel approach. It relies on a double Pummerer rearrangement on dithiacyclophane precursors, followed by ring contraction through a photochemical sulfur extrusion, and it is compatible with aryl moieties possessing very different e...
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A high yielding rearrangement of epoxy-esters, under Lewis acid conditions, to give bicyclic ortho esters is reported.
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Attack of cellular thiols on the antitumor natural product leinamycin is believed to generate a sulfenate intermediate that undergoes subsequent rearrangement to a DNA-alkylating episulfonium ion. Here, 2-(trimethylsilyl)ethyl sulfoxides were employed in a fluoride-triggered generation of sulfenate anions related to the putative leinamycin-sulfenate. The resulting sulfenates enter smoothly into...
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ژورنال
عنوان ژورنال: Chemistry Letters
سال: 1984
ISSN: 0366-7022,1348-0715
DOI: 10.1246/cl.1984.1831