Synthesis and structure of ansa-cyclopentadienyl pyrrolyl titanium complexes: [(η5-C5H4)CH2(2-C4H3N)]Ti(NMe2)2 and [1,3-{CH2(2-C4H3N)}2(η5-C5H3)]Ti(NMe2)

Seo, Won Seok; Cho, Youn Jaung; Yoon, Sung Cheol; Park, Joon T.; Park, Younbong

doi:10.1016/s0022-328x(01)01187-1

Cited by 25 publications

(11 citation statements)

References 28 publications

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“…In an independent study, fulvene 121 was prepared by reacting pyrrole-2-carbaldehyde ( 122 ) with cyclopentadiene in the presence of pyrrolidine (Scheme ). Reduction with lithium aluminum hydride afforded the dihydrofulvene 123 , and this reacted with 122 and pyrrolidine to produce the tripyrrene analogue 124 as a mixture of isomers. Further reduction with lithium aluminum hydride gave carbatripyrrane analogues 125 , again as a mixture of isomers.…”

Section: True Carbaporphyrins Carbachlorins and Related Systemsmentioning

confidence: 99%

“…Further reduction with lithium aluminum hydride gave carbatripyrrane analogues 125 , again as a mixture of isomers. In the original study, 125 was used in the preparation of ansa -cyclopentadienyl pyrrolyl titanium complexes …”

Section: True Carbaporphyrins Carbachlorins and Related Systemsmentioning

confidence: 99%

“…The fully aromatic form 19a has three internal protons and is likely to act as a trianionic ligand, , but in 19b one of the protons has been relocated onto the external nitrogen and this behaves as a dianionic ligand. Complexes of structural type 132 have also been obtained with Pd(II), Pt(II), − Cu(II), , Mn(III), Co(II), Rh(IV), , and Mo(II) (Figure ). Silver(I) trifluoroacetate was found to react with tetraaryl NCPs to give silver(III) derivatives 133a (M = Ag), corresponding to tautomer 19a (Scheme ).…”

Section: N-confused Porphyrins and X-confused Heteroporphyrinsmentioning

confidence: 99%

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Carbaporphyrinoid Systems

2016

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Following immediately after the serendipitous discovery of N-confused porphyrins, remarkably diverse carbaporphyrinoid systems have been synthesized and investigated. By replacing a pyrrolic unit within the porphyrin framework with cyclopentadiene, indene, azulene, cycloheptatriene, or benzene, new families of porphyrin-like macrocycles were produced. True carbaporphyrins are fully aromatic structures, while benziporphyrins are essentially devoid of macrocyclic aromatic character, and azuliporphyrins fall midway between the two extremes. Monocarbaporphyrinoids are superior organometallic ligands and form stable complexes with copper(III), silver(III), gold(III), nickel(II), palladium(II), platinum(II), rhodium(III), iridium(III), and ruthenium(II). Unusual oxidation reactions have also been discovered, commonly leading to derivatization of the internal carbon atom. In addition, structural rearrangements have been uncovered that allow the conversion of azuliporphyrins into benzocarbaporphyrins, and benziporphyrins into carbaporphyrins. Although less well studied, many examples of dicarbaporphyrinoids have been reported, and these show equally intriguing characteristics. Furthermore, contracted and expanded carbaporphyrinoids have been investigated. Studies in this area provide fundamental insights into the aromatic properties, tautomerization, and reactivity of porphyrins and related macrocyclic systems.

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Section: True Carbaporphyrins Carbachlorins and Related Systemsmentioning

confidence: 99%

Section: True Carbaporphyrins Carbachlorins and Related Systemsmentioning

confidence: 99%

Section: N-confused Porphyrins and X-confused Heteroporphyrinsmentioning

confidence: 99%

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Carbaporphyrinoid Systems

2016

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“…We have taken advantage of the synthetic method of Seo et al to produce a mixture of isomeric carba analogues of tripyrrane 8 a and 8 b, used previously as a suitable ligand to form ansacyclopentadienylpyrrolyltitanium complexes. [16] The synthesis involves the one-pot reaction of 2,5bis(mesitylhydroxymethyl)thiophene (9) with 8 in a 3 % solution of ethanol in chloroform, catalyzed by BF 3 ·Et 2 O, followed by oxidation with p-chloranil (tetrachloro-1,4-benzoquinone; Scheme 3). The procedure follows the [3+1] method previously utilized for the synthesis of heteroporphyrinoids and carbaporphyrinoids.…”

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confidence: 99%

Towards True Carbaporphyrinoids: Synthesis of 21‐Carba‐23‐thiaporphyrin

et al. 2014

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“…In this case the unsubstituted Cp is derivatized with two pyrrole groups which can both also coordinate to the central metal (98). [62] Christopherse tal. reported the targeted synthesis of a3tert-butyl-1-stannylpropyl Cp in three steps startingf rom tBuCp with good overall yields (99).…”

Section: Twofold-substituted Cpsmentioning

confidence: 99%

Synthetic Routes towards Multifunctional Cyclopentadienes

Frei

2019

Chemistry A European J

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Cyclopentadiene, and more importantly its functionalized derivatives, are a cornerstone of synthetic chemistry. Nowadays, they find applications in (chiral) catalysis, as ligands for organometallic complexes with potential diagnostic and therapeutic applications, and many more. This Minireview highlights the progress that has been made in the development of flexible and robust synthetic routes towards multifunctional cyclopentadienes in the last 20 years.

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Synthesis and structure of ansa-cyclopentadienyl pyrrolyl titanium complexes: [(η5-C5H4)CH2(2-C4H3N)]Ti(NMe2)2 and [1,3-{CH2(2-C4H3N)}2(η5-C5H3)]Ti(NMe2)

Cited by 25 publications

References 28 publications

Carbaporphyrinoid Systems

Carbaporphyrinoid Systems

Towards True Carbaporphyrinoids: Synthesis of 21‐Carba‐23‐thiaporphyrin

Synthetic Routes towards Multifunctional Cyclopentadienes

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