A selenonium ylid

Lloyd, Douglas R.; Singer, M. I. C.

doi:10.1039/c1967000390a

Cited by 10 publications

(12 citation statements)

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“…Recently, Lloyd and coworkers have prepared a series of heteronium ylides of groups V and VI including selenium and tellurium [5,13,14]. Monoylides of arsenic are found thermally quite unstable materials [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Ylide character and stability of heterocyclic benzenes

Kassaee

Vessally

Pirelahi

et al. 2008

Heteroatom Chemistry

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Section: Introductionmentioning

confidence: 99%

“…Ylides may form via connecting a carbon atom carrying an unshared pair of electrons with phosphorus [1], nitrogen [2], sulfur [3], arsenic [4], or selenium [5]. Phosphorus ylides, discovered by Staudinger and Meyer in 1919 [6], are used in the Wittig reactions [7].…”

Section: Introductionmentioning

confidence: 99%

Ylide character and stability of heterocyclic benzenes

Kassaee

Vessally

Pirelahi

et al. 2008

Heteroatom Chemistry

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“…1,2,3,4-Tetraphenyl 1,3-cyclopentadiene (Acros, Morris Plains, NJ, USA), p-toluenesulfonylhydrazide (Aldrich, St. Louis, MO, USA), diphenyl selenide (Alfa-Aesar, Heysham, UK), linalool (MerckSchuchardt), and solvents were used as such. Selenonium ylide was prepared by the method of Lloyd and Singer [27].…”

Section: Methodsmentioning

confidence: 99%

Kinetic study of copolymerization of linalool and methyl methacrylate initiated by selenonium ylide

Singh

Dwivedi

Singh

2010

Int J of Chemical Kinetics

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Free radical copolymerization of an acyclic monoterpenoid linalool (LIN) and methyl methacrylate (MMA) in dioxan was carried out in dilatometer under an inert atmosphere of nitrogen for 90 min at 60 ± 1 • C by using diphenyl selenonium 2,3,4,5-tetraphenylcyclopentadienylide (selenonium ylide) as an initiator. The kinetic expression of the reaction is R p ∝ [ylide] 0.5 [MMA] 1.0 [LIN] 1.0 . The activation energy of copolymerization was estimated to be 43.7 kJ mol −1 . The formation of a functional copolymer is evidenced by spectral analysis. The copolymer was characterized by FTIR, 1 H NMR, 13 C NMR, DSC, and TGA analysis.

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“…In fact, the first attempt to isolate selenonium ylide as a stable chemical entity was unsuccessful. It was found that the action of aqueous alkali or ammonia on fluorenyl-9-dimethylselenonium bromide 5 gave the expected selenonium ylide 6 as a black solid product, which after dissolving in organic solvents, decomposed rapidly with the evolution of dimethyl selenide even at room temperature (Scheme 1) [21]. It was not until more than 30 years ago that the first stable selenonium ylide 7 (Figure 4) was isolated and fully characterized (for details, see section 3-Synthesis) [22].…”

Section: Structural Featuresmentioning

confidence: 99%