Cyclomanganated derivatives of triphenylphosphine chalcogenides

Depree, Gary J.; Childerhouse, Nicholas D.; Nicholson, Brian K.

doi:10.1016/s0022-328x(96)06835-0

Cited by 24 publications

(25 citation statements)

References 35 publications

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“…When a mixture of the azabutadiene and PhCH 2 Mn(CO) 5 was slowly heated in heptane, no change was observed until the temperature of the oil bath reached 70°C, at which time two new IR peaks appeared at 2034 and 2076 cm -1 . The former of these can be attributed to the pyrrolinonyl complex 7, while the latter is in the position expected for the highest frequency v(CO) band for the 13 cyclometallated azabutadiene 5b (c.f.…”

Section: Methodsmentioning

confidence: 99%

“…All reactions were carried out under nitrogen, but no precautions to exclude air were taken during work-up. 4 The azabutadiene 4-phenyl-1-p-tolyl-1-azabuta-1,3-diene 3a, its 1,4-diphenyl analogue and PhCH 2 Mn(CO) 5 were prepared by literature routes [20,21]. PLC and TLC refer to preparative and thin layer chromatography on silica gel (Merck Kieselgel 60 PF 254 ).…”

Section: Generalmentioning

confidence: 99%

“…When the azabutadiene 3a was reacted with PhCH 2 Mn(CO) 5 , under the refluxingheptane conditions used successfully for cyclometallation of chalcones, a yellow product was readily isolated. Elemental analysis and ESMS were consistent with the expected product, a cyclometallated azabutadiene, but the infrared spectrum was not since the (CO) pattern was more like that of a Mn(CO) 3 moiety than the characteristic Mn(CO) 4 type.…”

Section: Attempted Cyclomanganation Of 4-phenyl-1-p-tolyl-1-azabuta-1mentioning

confidence: 99%

“…Substrates that have been examined include aryl-and hetero-aryl ketones [2] and imines [3], benzylamines [4], triphenylphosphine chalcogenides [5] and triphenylphosphine imines [6]. These complexes undergo a series of interesting reactions involving the Mn-C bond with alkenes [7], alkynes [8], organic isocyanates [9], sulfur dioxide [10] and carbon disulfide [11].…”

Section: Introductionmentioning

confidence: 99%

“…More recently, cyclomanganation studies have been extended beyond aryl substrates to reactions involving , -unsaturated ketones (chalcones) where compounds of the type 2 could be formed [12]. These also reacted with alkynes, in particular, to give novel products, including 5 -pyranyl-and 5 -cycloheptadienyl-Mn(CO) 3 derivatives [13].…”

Section: Introductionmentioning

confidence: 99%

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Manganese carbonyl-mediated reactions of azabutadienes with phenylacetylene, methyl acrylate and other unsaturated molecules

Mace¹,

Main²,

Nicholson³

et al. 2004

Journal of Organometallic Chemistry

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SynopsisPhCH 2 Mn(CO) 5 reacts with 1,4-di-aryl-1-aza-1,3-butadienes in the presence of unsaturated substrates to give products based on a cyclomanganated intermediate.PhCH 2 Mn(CO) 5PhC CH PhNCO CH 2 =CHCOOMe CO 2 Abstract.Reaction of PhCH 2 Mn(CO) 5 with 1,4-di-aryl-1-aza-1,3-butadienes gave substituted pyrrolinonyl rings which were 4 -coordinated to a Mn(CO) 3 group. These are formed by intramolecular CO insertion into a (non-isolated) cyclomanganated intermediate, followed by cyclisation. Other unsaturated reagents (PhC>CH, CH 2 =CHCOOMe, PhNCO) gave products arising from insertion of these, including a structurally characterised tri-aryl-5 -azacyclohexadienyl-Mn(CO) 3 complex from the reaction with the alkyne.

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Section: Methodsmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: Attempted Cyclomanganation Of 4-phenyl-1-p-tolyl-1-azabuta-1mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Manganese carbonyl-mediated reactions of azabutadienes with phenylacetylene, methyl acrylate and other unsaturated molecules

Mace¹,

Main²,

Nicholson³

et al. 2004

Journal of Organometallic Chemistry

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Manganese: Organometallic Chemistry

Sweigart

Reingold

2005

Encyclopedia of Inorganic Chemistry

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Ever since the characterization of Mn 2 (CO) 10 in 1954, manganese has played an important role in the development of organometallic chemistry. In some ways, however, manganese has not been as prominently utilized in synthesis and catalysis as some other transition metals such as iron, cobalt, chromium, and so on. The low cost of the metal, its accessible oxidation states, and the versatility of its many reaction pathways suggest that manganese will play a feature role in the organometallic chemistry of the future. Herein, new developments in organomanganese chemistry are described. There have been significant advances in insertion reactions, nucleophilic additions to coordinated arenes, and the chemistry of manganese‐coordinated carbenes, vinylidenes, and cymantrenes. Of special interest are the recent demonstration of manganese‐mediated activation of strong covalent bonds in sulfur and nitrogen heterocycles and the construction of organomanganese coordination networks via self‐assembly of modular quinonoid complexes.

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Mass Spectrometry and Gas‐Phase Ion Chemistry of Organomanganese Complexes

Palii

Zagorevskii

2011

Patai's Chemistry of Functional Groups

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This review (782 references) represents an exhaustive up‐to‐date survey of literature on mass spectrometry and gas‐phase ion chemistry of organomanganese complexes. Fundamental physico‐chemical characteristics of organomanganese ionic species, as well as the gas‐phase reactions resulting in the dissociation or formation of manganese‐carbon bond(s) are examined. Circa 300 examples of ion/molecule reactions characterizing the reactivity of Mn + , positively or negatively charged manganese clusters, as well as neutrals, cations and anions of various Mn‐containing species (including coordinatively unsaturated ones) are summarized. A variety of studies involving tandem mass spectrometry, neutralization‐reionization mass spectrometry, collision‐induced dissociation, multiple‐photon dissociation, IRMPD spectroscopy and theoretical calculations for organomanganese ion structure characterization are discussed. Additionally, analytical applications of mass spectrometric techniques to the characterization of compounds containing a MnC bond are reviewed. These include a number of relatively simple mononuclear complexes, polynuclear clusters, complexes incorporating organometallic units bridged with organic fragment(s), bifunctional compounds containing organometallic and classical Werner‐type coordination sites, fullerenes or planar polyaromatic hydrocarbons with an organomanganese fragment attached to them, manganospiralenes, manganoscorpionates, supramolecular entities, cymantrene‐peptide bioconjugates, etc.

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Cyclomanganated derivatives of triphenylphosphine chalcogenides

Cited by 24 publications

References 35 publications

Manganese carbonyl-mediated reactions of azabutadienes with phenylacetylene, methyl acrylate and other unsaturated molecules

Manganese carbonyl-mediated reactions of azabutadienes with phenylacetylene, methyl acrylate and other unsaturated molecules

Manganese: Organometallic Chemistry

Mass Spectrometry and Gas‐Phase Ion Chemistry of Organomanganese Complexes

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