(.eta.6-Polyarene)Mn(CO)3+ Complexes as Manganese Tricarbonyl Transfer Reagents. A Convenient and General Synthetic Route to (arene)Mn(CO)3+ Complexes

Sun, Shouheng; Yeung, Lee K.; Sweigart, Dwight A.; Lee, Tae Young; Lee, Su Seong; Chung, Young Keun; Switzer, Susan R.; Pike, Robert D.

doi:10.1021/om00006a001

Cited by 92 publications

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“…As with complex 1a, complexes 2a Á/6a were easily made as the BF ( 4 salt by reaction of the appropriate hydroquinone ligand with the manganese tricarbonyl transfer reagent [(h 6 -acenaphthene)Mn(CO) 3 ]BF 4 [5]. Complexes 2aÁ/6a are very stable in solution and in the solid state and were fully characterized by IR and NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl

Oh¹,

Reingold²,

Carpenter³

et al. 2003

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl

Oh¹,

Reingold²,

Carpenter³

et al. 2003

Journal of Organometallic Chemistry

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“…This is generally not difficult, but nevertheless does constitute a required step. [8] Second, it is necessary to remove the activating group after the reaction, and to recover it if the overall process is to be made catalytic. Third, the presence of an activating group may render sites other than those desired to be accessible to nucleophilic attack.…”

Section: à C Bond Activationmentioning

confidence: 99%

The Remote Activation of Chemical Bonds via Metal Coordination

Oh¹,

Yu²,

Li³

et al. 2003

Adv Synth Catal

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“…2 Methods have been developed for this oxidation using ruthenium, 28 iridium, rhodium, and palladium salts and hydrogen peroxide, 29 hypervalent iodine reagents, 30 nitric acid and acetic acid in air, 31 and vanadyl acetylacetonate and hydrogen peroxide. 32 One report detailed the synthesis of 1,4-dihydroanthracene from anthracene via a series of brominations and oxidations.…”

Section: Methodsmentioning

confidence: 99%

“…28 As with the cyclohexadiene analogs, the initially formed coordination diastereomer ratio of the isolated mixture is low (2.3:1). Protonation of this mixture produces a single diastereomer of the allyl complex 13.…”

Section: C1mentioning

confidence: 97%

“…Reactions on anthracene, especially on the terminal ring, are possible when it is complexed to {TpW(NO)(PMe 3 )}, unlike when it is complexed to Mn(CO) 3 , on which the anthracene is prone to slipping off. 28,29 While the double nucleophilic addition appears promising for a nice range of nucleophiles, the fact that the first and second nucleophiles must be the same is a limitation of this method for anthracene functionalization.…”

Section: Scheme 18mentioning

confidence: 99%

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Reactivity and Functionalization of Naphthalene and Anthracene Complexes of {TpW(NO)(PMe3)}

Strausberg¹

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Chapter 1 introduces the organic chemistry of aromatic hydrocarbons, with attention paid to regiochemical outcomes of organic reactions. The binding of naphthalene and anthracene to metal complexes is discussed, along with organic transformations they undergo as a result of their complexation. The previous work on osmium and rhenium complexes of naphthalene from the Harman group is explored. Finally, some spectroscopic techniques for exploring the chemistry of {TpW(NO)(PMe 3 )} complexes of naphthalene and anthracene are introduced.Chapter 2 discusses the highly distorted allyl complexes formed from {TpW(NO)(PMe 3 )} and the exploration of their origin. Attempts at stereoselectively deprotonating these cationic complexes is also discussed.Chapter 3 describes our study of TpW(NO)(PMe 3 )(3,4-η 2 -naphthalene)'s ability to undergo a Diels-Alder reaction with N-methylmaleimide. A solvent study suggested that this reaction proceeds by a concerted mechanism. To probe the mechanism further, we synthesized a series of methylated and methoxylated naphthalene complexes and measured their rates of reaction with N-methylmaleimide compared to the parent complex. We found that 1-substitution on the naphthalene increased the rate of cycloaddition, even if the substituent was in the unbound ring, while 2-substitution slowed the reaction rate when in the bound ring. This information is consistent with a concerted mechanism, as a 2-substituted product would be less able to isomerize to form the active isomer for the cycloaddition to occur.Chapter 4 discusses tandem electrophile and nucleophile additions to

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(.eta.6-Polyarene)Mn(CO)3+ Complexes as Manganese Tricarbonyl Transfer Reagents. A Convenient and General Synthetic Route to (arene)Mn(CO)3+ Complexes

Cited by 92 publications

References 0 publications

Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl

Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl

The Remote Activation of Chemical Bonds via Metal Coordination

Reactivity and Functionalization of Naphthalene and Anthracene Complexes of {TpW(NO)(PMe3)}

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