The versatile chemistry of arenemanganese carbonyl complexes

Sun, Shouheng; Dullaghan, Conor A.; Sweigart, Dwight A.

doi:10.1039/dt9960004493

Cited by 57 publications

(35 citation statements)

References 70 publications

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“…Yield: 0.05 g, 66.80%. Single crystals suitable for X-ray diffraction were obtained via the slow evaporation of a C 6 …”

Section: [(G 6 -Flu * H)mn(co) 3 ]Pf 6 (1)mentioning

confidence: 99%

“…The majority of examples in the literature refer to AreneCr(CO) 3 derivatives, and these have found many uses in organic synthesis, especially in the highly selective preparation of substituted cyclohexadienes [1][2][3][4]. An increasing number of Arene MnðCOÞ þ 3 complexes have now been isolated, and their use in both the synthesis of useful organic compounds and other organometallic complexes is beginning to be exploited [2,5,6].…”

Section: Introductionmentioning

confidence: 99%

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The synthesis of [(η6-Flu∗H)Mn(CO)3]PF6, and its deprotonation to yield a novel coordination mode of fluorene

Moss

Thomas

Cowley

et al. 2007

Journal of Organometallic Chemistry

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“…Yield: 0.05 g, 66.80%. Single crystals suitable for X-ray diffraction were obtained via the slow evaporation of a C 6 …”

Section: [(G 6 -Flu * H)mn(co) 3 ]Pf 6 (1)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The synthesis of [(η6-Flu∗H)Mn(CO)3]PF6, and its deprotonation to yield a novel coordination mode of fluorene

Moss

Thomas

Cowley

et al. 2007

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…Regioselectivity is also dependent on the electronic nature of the nucleophile. Most remarkably, addition of the primary sulfur-stabilized anion shows nearly equal (29) (30) amounts of ortho and meta substitution with the toluene ligand, but, as the size of the arene substituent increases, the para substitution product increases at the expense of the meta product (entries [10][11][12]. The dependence of selectivity on anion type and ring substituent is understood as a change in the balance of charge vs orbital control [2].…”

Section: Regioselectivity In O-disubstituted Arenes Is Often High Andmentioning

confidence: 99%

“…If a hydrogen occupies the ipso position, oxidation of the intermediate gives formal nucleophilic substitution for hydrogen (3, path b). General reviews have appeared [1][2][3][4] as well as others with an emphasis on h 6 -arene-Cr(CO) 3 complexes [5,6], on h 6 -arene-FeCp + (Cp=h 5 -cyclopentadienyl) complexes [7][8][9], h 6 -arene-RuCp + [10,11], and on h 6 -arene-Mn(CO) 3 complexes [12]. The purpose of this chapter is to summarize the established or potential synthesis methodology available via nucleophile addition to a metal-coordinated arene ligand.…”

Section: Introductionmentioning

confidence: 99%

(Arene)Cr(CO)3 Complexes: Aromatic Nucleophilic Substitution

Semmelhack

Chlenov

2004

Topics in Organometallic Chemistry

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Transition metals coordinated to the pi system of arenes function as strong electronwithdrawing groups and favor nucleophilic addition to the arene to give cyclohexadienyl-metal complexes. The regioselectivity of addition is influenced in subtle and indirect ways, compared to the powerful effect on both reactivity and regioselectivity of electron-withdrawing groups attached to the sigma bond system of the arene. The intermediate cyclohexadienyl complexes can be processed in several ways, leading to several distinct synthesis methods. Useful reactivity is known for several metal systems and each is discussed for specific reaction types. The presence of a fluoro or chloro substituent on the arene allows an effective analog of classical S N Ar reactivity, with a wide range of nucleophiles including simple amines, alkoxides, and carbon anions. Another general process is the addition/protonation protocol, where a hydrogen substituent on the arene is replaced by a nucleophile. This opens new questions of regioselectivity since the typical arene ligand has several hydrogens which are candidates for substitution. The formation of five-and six-membered rings by both general mechanisms are known. Less general indirect mechanisms (e.g., tele substitution) have also been defined.

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“…Among these the two possible stereoisomeric tris-complexes were characterized [131]. Recently, cationic tricarbonylmanganese complexes of several centropolyindanes have been prepared and their structures characterized [132].…”

Section: Scheme 56 Miscellaneous Derivatives Of Centropolyindanesmentioning

confidence: 99%

The Centropolyindanes and Related Centro-Fused Polycyclic Organic Compounds

Kuck

1998

Topics in Current Chemistry

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Centropolyindanes constitute a complete family of arylaliphatic polycyclic hydrocarbons containing several indane units. Mutual fusion of the five-membered rings leads to three-dimensional, carbon-rich molecular frameworks bearing a central carbon atom, such as benzoannelated [3.3.3]propellanes, triquinacenes, and [5.5.5.6]-and [5.5.5.5]fenestranes. In this review, the structural concept of centropolyindanes is contrasted to other fused indane hydrocarbons. Besides the syntheses of the parent centropolyindanes and recently described related indane hydrocarbons, the preparation of a large variety of bridgehead and arene substituted centropolyindanes is presented including strained, heterocyclic, and centrohexacyclic derivatives. In appropriate cases, the particular reactivity and some structural features of these unusual, sterically rigid polycyclic compounds are pointed out.

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The versatile chemistry of arenemanganese carbonyl complexes

Cited by 57 publications

References 70 publications

The synthesis of [(η6-Flu∗H)Mn(CO)3]PF6, and its deprotonation to yield a novel coordination mode of fluorene

The synthesis of [(η6-Flu∗H)Mn(CO)3]PF6, and its deprotonation to yield a novel coordination mode of fluorene

(Arene)Cr(CO)3 Complexes: Aromatic Nucleophilic Substitution

The Centropolyindanes and Related Centro-Fused Polycyclic Organic Compounds

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