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Synthesis of novel trithiocarbonate-S-oxides
KTH, Superseded Departments, Chemistry.
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2003 (English)In: Phosphorus Sulfur and Silicon and the Related Elements, ISSN 1042-6507, E-ISSN 1563-5325, Vol. 178, no 11, 2403-2413 p.Article in journal (Refereed) Published
Abstract [en]

The oxidation of the trithiocarbonates 3 with m-chloroperoxybenzoic acid (m-CPBA) in chloroform at room temperature provides an efficient stereoselective synthesis of the (E) sulfine 4(a) and (Z) sulfine 4(b). The expected (E) and (Z) configurations of 4(a,b) were confirmed by x-ray structure determination. The Sulfines 4 were further structurally elucidated by their cycloaddition reactions with 2,3-dimethyl-1,3-butadiene in chloroform at room temperature to give the corresponding dihydrothiopyran S-oxides 5(a,b) in a quantitative yield.

Place, publisher, year, edition, pages
2003. Vol. 178, no 11, 2403-2413 p.
Keyword [en]
chlorodithioformates, dihydrothiopyran-S-oxide, oxidation, sulfines, trithiocarbonate, aliphatic sulfines, convergent synthesis, thiophilic addition, silyl thioketones, chemistry, oxidation, organolithiums
Identifiers
URN: urn:nbn:se:kth:diva-22986ISI: 000186779000011OAI: oai:DiVA.org:kth-22986DiVA: diva2:341684
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10Bibliographically approved

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