Journal ArticleDOI
Heterocyclic phosphonium salts by reaction of dimethyl(1,2-alkadienyl)-phosphine oxides with electrophilic reagents
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TLDR
In this paper, the essential influence of tertiary carbenium ions for realization of oxaphospholic cyclization of phosphorylated allenes has been established, and the reaction of dimethyl(1,2-alkadienyl)phosphine oxides with halogens, sulfenyl and selenenyl chlorides.Abstract:
Salts of 2,5-dihydro-1,2-oxaphosphole have been prepared by reaction of dimethyl(1,2-alkadienyl)phosphine oxides with halogens, sulfenyl and selenenyl chlorides. The essential influence of tertiary carbenium ions for realization of oxaphospholic cyclization of phosphorylated allenes has been established.read more
Citations
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Journal ArticleDOI
Stereospecific reduction of phosphine oxides to phosphines by the use of a methylation reagent and lithium aluminum hydride.
TL;DR: Optically active P-chirogenic phosphine oxides are reduced with inversion of configuration at phosphorus atom by treatment with methyl triflate, followed by reaction with LiAlH4.
Journal ArticleDOI
Redox-neutral organocatalytic Mitsunobu reactions
Rhydian H. Beddoe,Keith G. Andrews,Valentin Magné,James D. Cuthbertson,Jan Saska,Andrew L. Shannon-Little,Stephen E. Shanahan,Helen F. Sneddon,Ross M. Denton +8 more
TL;DR: It is demonstrated that a specially designed phosphine oxide promotes nucleophilic substitution reactions of primary and secondary alcohols in a redox-neutral catalysis manifold that produces water as the sole by-product.
Journal ArticleDOI
2,5-dihydro-1,2-oxaphospholene derivatives by the reaction of 1,2-alkadienephosphonates and phosphorus pseudohalogenes
TL;DR: In this paper, the interaction of 1,2-aIkadienephosphonic derivatives with phosphorus containing pseudohalogenes affords 2,5-dihydro-1,2oxaphospholene derivatives.
Journal ArticleDOI
Aryloxy derivatives of 3-methyl-1,2-butadienephosphonic acid and their oxaphospholic cyclization in the reactions with electrophilic reagents
TL;DR: In this paper, the preparation of aryloxy derivatives of 3-methyl-1,2-butadienephosphonic acid and their reactions with electrophilic reagents are investigated.
Journal ArticleDOI
A New Approach to 1-Substituted-1,2Alkadienephosphonates I
Dobromir D. Enchev,Marko Kirilov +1 more
TL;DR: In this article, the substitution of the H atom at the C 1 position of the phosphorylated allenes with different kind of electrophiles has been discussed and evidence for the mechanism of the heterocyclization of allenephosphonates by the reaction with electrophilic reagents has been supplied.
References
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Zh. Obshch. Khim.
A.V. Bogatskii,Sergei A. Andronati,Z. I. Zhilina,O. V. Kobzareva,P. A. Sharbatyan,R Ivanova,T. K. Chumachenko +6 more
Journal ArticleDOI
Five-membered heterocyclization of phosphorus-containing allenes by their reaction with electrophiles—possibilities and restrictions
TL;DR: In this paper, the authors generalize the results obtained so far, allowing a critical assessment of the conditions and restrictions for the realization of the cyclization of allenic system of π-bonds and phosphorylic group.
Journal ArticleDOI
Reaction of dimethyl esters of 3-methyl-1,2-alkadienephosphonic acids with methylsulfenyl chloride—orientation and stereochemistry
TL;DR: The reaction of 3-methyl-1,2-alkadienephosphonic acid (i.e. 3-alkyl-3-methylsubstituted allenephosphoric) dimethyl esters with methylsulfenyl chloride 2 is oriented mainly to the 1-2-oxaphosphol-3ene ring products 3a-d (as diastereoisomeric mixtures when alkyl ≠ CH3) as mentioned in this paper.
Journal ArticleDOI
Chemo-, regio- and stereoselectivity of the reaction of dialkyl-1,2-alkadienylphosphonates with selenenyl chlorides. 1,3-sigmatropic rearrangement of 2,3-adducts
TL;DR: In this article, the chemo-, regio-and stereoselectivity of the reaction of dialkyl-1,2-alkadienylphosphonates with selenenyl chlorides has been investigated.
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