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1.14 Three-membered Rings with Two Oxygen and/or Sulfur Atoms


Mlostoń, Grzegorz; Romanski, Jaroslaw; Heimgartner, Heinz (2022). 1.14 Three-membered Rings with Two Oxygen and/or Sulfur Atoms. In: Black, David. Comprehensive Heterocyclic Chemistry IV. Waltham, MA: Elsevier, 641-677.

Abstract

Combination of matrix isolation techniques with theoretical methods for identification and characterization of some dithiiranes and oxathiiranes is presented. In general, both dithiiranes and oxathiiranes were generated via flask vacuum pyrolysis of suitable sulfur-containing precursors such as 1,2,4-trithiolanes, 1,3-dithietane 1,3-dioxide or thiocarbonyl S-oxides (sulfines). Novel applications of dimethyldioxirane (DMDO) and (trifluoromethyl)methyl dioxirane (TFMDO) as versatile oxidizing reagents published in the period 2008–2018 are summarized. Methods applied for manufacturing of new polymeric materials functionalized with dioxirane moieties and reported in patents are presented. Mechanisms involving Criegee intermediates in reactions of carbonyl compounds with dioxiranes using experimental and theoretical methods are discussed in the light of recent results.

Abstract

Combination of matrix isolation techniques with theoretical methods for identification and characterization of some dithiiranes and oxathiiranes is presented. In general, both dithiiranes and oxathiiranes were generated via flask vacuum pyrolysis of suitable sulfur-containing precursors such as 1,2,4-trithiolanes, 1,3-dithietane 1,3-dioxide or thiocarbonyl S-oxides (sulfines). Novel applications of dimethyldioxirane (DMDO) and (trifluoromethyl)methyl dioxirane (TFMDO) as versatile oxidizing reagents published in the period 2008–2018 are summarized. Methods applied for manufacturing of new polymeric materials functionalized with dioxirane moieties and reported in patents are presented. Mechanisms involving Criegee intermediates in reactions of carbonyl compounds with dioxiranes using experimental and theoretical methods are discussed in the light of recent results.

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Additional indexing

Item Type:Book Section, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > General Engineering
Language:English
Date:2022
Deposited On:24 Feb 2020 12:20
Last Modified:10 Mar 2024 04:31
Publisher:Elsevier
ISBN:978-0-12-818656-5
OA Status:Green
Publisher DOI:https://doi.org/10.1016/B978-0-12-409547-2.14765-1