A new method for the synthesis of α,β-acetylenic phosphines

Трофимов, Б. А.; Brandsma, L.; Arbuzova, S. N.; Гусарова, Н. К.

doi:10.1007/bf02495235

Cited by 16 publications

(13 citation statements)

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“…Quenching the resulting deep red suspensions with water or butylhalides afforded mixtures of mostly primary or tertiary phosphanes as detectable products ( I , Scheme ; only Ph shown), but with only low selectivity and poor yields (0–40 %) in addition to large quantities of organopolyphosphines . Equally challenging with similar product mixtures are the reactions of P 4 with alkynyls ( II ) or with tert‐ butyl‐ or methyllithium in combination with Me 3 SiCl as quenching agent ( III ) . The more bulky reagents allowed for formation of cyclotetraphosphanes (e.g.…”

Section: Functionalization Of P4 Using Main Group Metal Organylsmentioning

confidence: 99%

Functionalization of P₄ through Direct P−C Bond Formation

Borger

Ehlers

Slootweg

et al. 2017

Chemistry A European J

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Research on chlorine‐free conversions of P4 into organophosphorus compounds (OPCs) has a long track record, but methods that allow desirable, direct P−C bond formations have only recently emerged. These include the use of metal organyls, carbenes, carboradicals, and photochemical approaches. The versatile product scope enables the preparation of both industrially relevant organophosphorus compounds, as well as a broad range of intriguing new compound classes. Herein we provide a concise overview of recent breakthroughs and outline the acquired fundamental insights to aid future developments.

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Section: Functionalization Of P4 Using Main Group Metal Organylsmentioning

confidence: 99%

Functionalization of P₄ through Direct P−C Bond Formation

Borger

Ehlers

Slootweg

et al. 2017

Chemistry A European J

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“…Hence, the reaction of cyanoacetylenic alcohols with secondary phosphines, that proceeds regio-and stereoselectively under mild conditions as trans addition of nucleophiles (specifically, P-nucleophiles [3,13]) to activated acetylenes [14], opens up a convenient and effective synthetic route to new functionalyzed tertiary phosphines, promising polydentate amphiphilic ligands for the design of catalysts of new generation [15,16], as well as highly reactive intermediates for fine organic synthesis.…”

Section: Iia!iic 76mentioning

confidence: 99%

Noncatalytic Regio- and Stereoselective Addition of Secondary Phosphines to Cyanoacetylenic Alcohols

et al. 2005

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Secondary phosphines regio-and stereoselectively add to 4-hydroxy-4-methyl-2-pentynenitrile, a typical and available representative of cyanoacetylenic alcohols, without catalyst at room temperature (THF, 3 h) to form (Z)-3-[dialkyl(aryl)phosphino]-4-hydroxy-4-methyl-2-pentenenitriles in 80385% yields. These compounds relate to a new class of functionalyzed phosphines, promising ligands for the design of metalcomplex catalysts.

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“…[24][25][26][27] This paper discusses new prospects for further development of the Trofimov-Gusarova reaction, which involve successful application of ionizing radiation (electromagnetic radiation in the X-ray and γ-ranges) for activation of elemental phosphorus and modifying its reactivity by means of controlled defect formation in its structure. [28][29][30][31] In solid-state physics and chemistry, the term "defect" (which is generally related to the anomaly of the phenomenon) assumes the meaning of a structural element which is different from the remaining regular portion of the substance and possesses specific local properties.…”

Section: Introductionmentioning

confidence: 99%