Erinnerungen an Arthur Lüttringhaus (1906−1992)

Prinzbach, Horst

doi:10.1002/(sici)1099-0690(199804)1998:4<735::aid-ejoc735>3.0.co;2-n

Cited by 4 publications

(2 citation statements)

References 73 publications

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“…The catenane strategy of Scheme was all but fully explored. This may have been a direct consequence of Lüttringhaus' decision to retire from Freiburg University's Chemistry Department in 1971 for good . The contents of Scheme were published as a communication in 1967 .…”

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

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Pioneering Work on Catenanes, Rotaxanes, and a Knotane in the University of Freiburg 1958–1988

Brückner

2019

Eur J Org Chem

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Research at the University of Freiburg is summarized which aimed at realizing catenanes, rotaxanes, and a molecular knot from 61–62 until 41 years ago. Taking a fresh view at ansa‐compounds – distinct from those in which he had been interested for other reasons before – Arthur Lüttringhaus began to tackle syntheses of catenanes in 1957. The first isolation of a pure catenane (37) succeeded in 1964 jointly with Gottfried Schill. Most of the progress made in the sequel was due to Schill alone or achieved under his direction; in addition, a few follow‐up studies were published without Schill or Lüttringhaus being their authors. The major feats of these endeavors were the syntheses of the following molecules: (1) the first catenanes (38 – de‐acetyl‐41, 74) without a ring in any constituent (this feature makes them unique till today; the catenane 74 holds the additional record of being the only all‐hydrocarbon catenane till now); the first [3]catenanes at all (obtained as a mixture of constitutional isomers C2v‐97 and C2h‐97); the first [3]catenanes exhibiting topological isomerism (89, iso‐89, and neo‐iso‐89); the rotaxanes 70 [which had the design peculiarity of being convertible into a catenane (74)], 113 (Schill's #1‐rotaxane), and 115; the pre‐knotane rac‐dia‐iso‐123 [provided it was obtained and not (only) its topological isomer dia‐iso‐123]. – For due perspectives, pertinent studies of third parties are included, too: 1) Wasserman's reports on the isolation of the catenane 8 are analyzed in great detail; the conclusion is that the identity of 8 was never established. 2) Schill's oscillating rotaxane 70 from 1988, which is subject to a reversible and non‐degenerate ring migration (→ iso‐70), is supplemented by Stoddart's much faster oscillating rotaxane 71 from 1991, which undergoes a reversible and degenerate ring migration (→ 71 instead of → iso‐71) and was dubbed “molecular shuttle”. 3) The first [3]catenanes from the groups of Schill (97; 1969), Sauvage (98 and 99; 1985), and Stoddart (100–102; 1991) are juxtaposed. 4) The Harrisons' synthesis of the rotaxane 106 by a most noteworthy solid‐phase approach (1967) is recalled in the context of Schill's synthesis of the rotaxane 113 (1967 or 1969). 5) Attempts at threading α‐cyclodextrin by long‐chain 1,ω‐dithiols (→ 130) and ring‐closing the latter oxidatively for obtaining catenated disulfides failed in Lüttringhaus' 1957/1958 studies; in contrast, Stoddart's threading permethyl‐β‐cyclodextrin (133) by the long‐chain 1,ω‐diamine 132 and ring‐closing the latter by a double condensation with terephthaloyl dichloride was successful by providing 3 % of the catenated bislactame 134 in 1993. The concluding section characterizes the synthetic strategies towards catenanes and rotaxanes developed in Freiburg as “template‐based”. This differs from the Nobel Prize Committee's assessment.

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Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

“…(ii) for being able to link Professor Lüttringhaus off‐handedly to “catenanes” and “Schill” upon Prinzbach's mentioning that he had earned his Ph. D. degree and habilitation in this man's laboratories.…”

Section: Introductionmentioning

confidence: 99%

Pioneering Work on Catenanes, Rotaxanes, and a Knotane in the University of Freiburg 1958–1988

Brückner

2019

Eur J Org Chem

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Anschauliche Bezeichnungen der Chemie von Metallocen‐Komplexen der Gruppe 4

Rosenthal

2020

Angewandte Chemie

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Drei Beispiele fürd ie Verwendung einfacher und anschaulicher Benennungen in der Organometallchemie von Metallocen-Komplexen der Gruppe 4w erden erklärt und diskutiert. Die Bezeichnung "tuck(ed)-in" betrifft das Verhalten des Decamethyltitanocens [(C 5 Me 5) 2 Ti]o der ähnlicher Komplexe,b ei dem eine oder zwei Methylgruppen Titanhydrid-Komplexew ie [(C 5 Me 5)(C 5 Me 4 CH 2)TiH] oder andere Hydridkomplexed urch C-H-Aktivierung bilden. In der "merrygo-round-reaction" wird die Umlagerung von C-Atomen am Titan in Organometallmolekülen beschrieben, bei der eine Rotation von zwei C-Atomen mit einer Rotation der sechsgliedrigen Dihydroindenyl-Einheit am Titan erfolgt. Das dritte Beispiel "migration" oder "tobogganing" betrifft das "sliding" von Titanocen an der Kette eines linearen Polyins durchK oordinierung von einer oder mehreren Dreifachbindungen. In allen diesen Reaktionen wechselt die Koordinationsweise des Metalls am Cp-oder dem Substratliganden, was mit einer intramolekularen Dynamik verbunden ist.

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Vivid Wording for the Chemistry of Group 4 Metallocene Complexes

Rosenthal

2020

Angew Chem Int Ed

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Three selected examples for the use of unusual wording to describe the organometallic chemistry of Group 4 metallocenes are explained and discussed. The term "tuck(ed)in" concerns the behavior of decamethyltitanocene [(C 5 Me 5) 2 Ti]a nd similar complexes in whicho ne or two methyl groups form the titanium hydride complex [(C 5 Me 5)-(C 5 Me 4 CH 2)TiH] or other hydride complexes by C À Hactivation. In the so-called "merry-go-round reaction" the rearrangement of Ca toms bound to titanium in organometallic molecules is described whichc orresponds to the rotation of two Catoms along with arotation of the six-membered ring in ad ihydroindenyl moiety at titanium. In the third example "migration" or "tobogganing" concerns the "sliding" of titanocene along the chain of alinear polyyne by coordination to one or more triple bonds.Inall these reactions changes of the coordination mode of the metal at Cp or substrate ligands by intramolecular dynamics occur.

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Erinnerungen an Arthur Lüttringhaus (1906−1992)

Cited by 4 publications

References 73 publications

Pioneering Work on Catenanes, Rotaxanes, and a Knotane in the University of Freiburg 1958–1988

Pioneering Work on Catenanes, Rotaxanes, and a Knotane in the University of Freiburg 1958–1988

Anschauliche Bezeichnungen der Chemie von Metallocen‐Komplexen der Gruppe 4

Vivid Wording for the Chemistry of Group 4 Metallocene Complexes

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