Journal ArticleDOI
Syntheses of 1,2-Thiaphospholes and Their Thermal and Lewis Acid-Promoted Addition Reactions
TLDR
In this article, 3,5-Di-substituted 1,2-thiaphospholes were efficiently prepared by treating 2,9-dithia-1-phosphabicyclo[4.3.0]nona-3,7-diene 1-sulfides with n-Bu3P.Abstract:
3,5-Di-substituted 1,2-thiaphospholes were efficiently prepared by treating 2,9-dithia-1-phosphabicyclo[4.3.0]nona-3,7-diene 1-sulfides with n-Bu3P. The thiaphospholes reacted thermally with norbornadiene, norbornene or diethyl azodicarboxylate to produce the 1 : 2 double Diels–Alder cycloadducts. With a mixture of norbornadiene and methyl acrylate or acrylonitrile, the crossed double Diels–Alder cycloadducts were obtained. In the presence of a Lewis acid, the thiaphospholes underwent, at the initial step, the Diels–Alder reaction with acrylic esters, methyl vinyl ketone or acrylonitrile, followed in tandem by the Michael addition of the 1 : 1 cycloadducts to another molecule of the reactant.read more
Citations
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Journal ArticleDOI
Cycloaddition reactions of heterophospholes
TL;DR: The cycloaddition reactions given by the heterophospholes, which are five-membered 6π aromatic heterocycles containing at least one σ2, λ3 phosphorus, are reviewed in the present article.
Journal ArticleDOI
Diels–Alder reactions involving CP– functionality
Book ChapterDOI
4.3 – Heterophospholes
TL;DR: In this article, the authors discuss the 671-systems with one or more two-coordinate phosphorus atoms in the ring and the remaining 42 systems with two and more heteroatoms besides phosphorus, including aza-and thiadiphospholes, diazadiphophospholes and azaphosphaarsoles.
Book ChapterDOI
The Coordination Chemistry of Phosphinines: Their Polydentate and Macrocyclic Derivatives
Book ChapterDOI
Six-membered Rings: Phosphinines
TL;DR: In this paper, the authors remark that the real landmark of low-coordinated phosphorus compounds was set when Markl reported in 1966 the successful preparation of triphenylphosphinine from the reaction between a source of PH3 and the corresponding pyrylium salt.
References
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Journal ArticleDOI
2-chlor-1-thia-2-phosphirane - synthese und reaktionen - hinweise für den 1,3-dipol
Gottfried Märkl,W. Hölzl +1 more
TL;DR: In this paper, the title compounds were obtained by reaction of 5-methyl-1,3,4-oxathiazol-2-one with phosphaalkenes, and the intermediate formation of the P-analog of nitrilsulfides (via the thiaphosphirenes) as 1,3-dipoles were presented.
Journal ArticleDOI
1,2, 4λ3-thiaazaphosphole, 1,2λ3, 4λ3-thiadiphosphole und 1,2λ3-thiaphosphole aus 1,3,4-oxathiazol-2-onen und phosphaalkenen
Gottfried Märkl,W. Hölzl +1 more
TL;DR: In this paper, the title compounds are described for the first time and are the result of (3+2)- and (4+2) cycloaddition reactions with phosphaalkenes.
Journal ArticleDOI
Chemistry of 1,2-Thiaphosphole 2-Sulfides. III. Cycloaddition Reactions with Some Acetylenic Dienophiles and Generation of Phosphorin 1-Sulfides
Hideyuki Tanaka,Shinichi Motoki +1 more
TL;DR: In this article, 1,2-Thiaphosphole 2-sulfides reacted with dimethyl acetylenedicarboxylate or phenylacetylene to afford 1-phosphabarrelene 1-Sulfides via phosphorin 1Sulfide.
Journal ArticleDOI
2,9-dithia-1-thioxophosphabicyclo[4.3.0]nona-3,7-dienes. Precursors of new type heterodienes, 2-thioxo-1,2-thiaphospholes
TL;DR: In this paper, arylmethylenepinacolones, chalcones and 2-arylmethylene-1-tetralones with P 4 S 10 in the presence of triethylamine gave the title compounds, from which 2-thioxo-1,2-thiaphospholes (phosphathiophenes) were generated by the thermolysis and reacted with acrylonitrile to give [4+2]cyclo-adducts.
Journal ArticleDOI
Chemistry of 1,2-thiaphosphole 2-sulfides. I. Cycloaddition reactions of 1,2-thiaphosphole 2-sulfides with some dienophiles.
TL;DR: In this article, 1,2-Thiaphosphole 2-sulfides generated by the thermolysis of the phosphabicyclo compounds underwent cycloaddition reactions with acrylonitrile, styrene, butyl vinyl ether and norbornene to give the [4+2]cycloadducts, respectively.