1998
DOI: 10.1055/s-1998-1939
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Synthesis of 1-Alkene-1,3-Sultones from 2,3-Epoxy-Alkanesulfonyl Chlorides

Abstract: Dehydrochlorination of α,β-epoxy sulfonyl chlorides 3 leads to 1-alkene-1,3-sultones 1 most probably via epoxy sulfenes 2.1-Alkene-1,3-sultones (1,2-oxathiole-2,2-dioxides) 1 are interesting compounds for synthetic exploration. In fact three places of nucleophilic attack can be envisaged for these α,β−unsaturated γ-sultones,viz. at sulfur, at C 4 (Michael addition) and at C 5 (sulfonate displacement). Surprisingly, the chemistry of unsaturated γ-sultones received little attention in the literature. 1 Compounds… Show more

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Cited by 17 publications
(3 citation statements)
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“…Because sultones are synthetically very useful heterocycles in organic synthesis, many groups are currently working on sultone chemistry. Most of the earlier procedures for sultone synthesis involved either carbanion-mediated sulfonate intermolecular or intramolecular coupling reactions (CSIC reactions) or sulfonation of olefins with dioxane–sulfur trioxide. Recently, many powerful methodologies have been developed for the synthesis of the sultones, such as intramolecular Diels–Alder reactions, ring-closing metathesis, Pd-catalyzed intramolecular coupling reactions, Rh-catalyzed C–H insertion, Rh-catalyzed carbene cyclization cycloaddition cascade reactions, etc.…”
Section: Synthesis Of Sultonesmentioning
confidence: 99%
“…Because sultones are synthetically very useful heterocycles in organic synthesis, many groups are currently working on sultone chemistry. Most of the earlier procedures for sultone synthesis involved either carbanion-mediated sulfonate intermolecular or intramolecular coupling reactions (CSIC reactions) or sulfonation of olefins with dioxane–sulfur trioxide. Recently, many powerful methodologies have been developed for the synthesis of the sultones, such as intramolecular Diels–Alder reactions, ring-closing metathesis, Pd-catalyzed intramolecular coupling reactions, Rh-catalyzed C–H insertion, Rh-catalyzed carbene cyclization cycloaddition cascade reactions, etc.…”
Section: Synthesis Of Sultonesmentioning
confidence: 99%
“…The epoxide 289 can be cyclized with triethylamine to give the 1,2-oxathiolane-2,2-dioxides 290 (Scheme 11.93) [240]. Most reactions in this area have involved either 1,2-oxathiolane 2-oxides or 2,2-dioxides.…”
Section: Introductionmentioning
confidence: 99%
“…Surprisingly, the chemistry of sultone 1 has received little attention in the literature. [1][2][3] As part of our research on 1,3-dipolar cycloaddition reactions, we were interested in utilizing sulfur-containing functionalities as activating groups in the design of dipolarophiles. Recently, the cycloaddition reaction of sultone 1 with nitrile oxides has been accomplished by us with satisfactory results.…”
Section: Introductionmentioning
confidence: 99%