Aliphatic 1,2,3‐Triketones by Ozonolysis of Dialkyl‐1,4‐benzoquinones

Schill, Gottfried; Logemann, Enno; Zürcher, Clemens

doi:10.1002/anie.197210891

Cited by 4 publications

(11 citation statements)

References 6 publications

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“…In preparation thereof, Schill's groups had undertaken model ozonolyses of simpler hydroxyquinones (and desoxygenated one of their ozonolysis products in the sequel completely for modeling the steps 25–27 of Scheme ) . With the “real compound”, that is the hydroxyquinone‐containing catenane N ‐acetyl‐ 36 of Scheme , ozone reacted in a surprising variety of manners.…”

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

“…Correct catenane combustion analyses were reported for the final product 37 ,, for N ‐acetyl‐ 36 (neutral catenane from step 22 of Scheme ),, and for N , O ‐diacetyl‐ 36 (neutral catenane from step 21) , . In 1972, the catenane 37 was carried on to the first “catenane without a ring in either constituent” ever, namely to compound 41 of Scheme .…”

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

“…Conversion of catenane N , O ‐diacetyl‐ 36 (synthesis: Scheme ) into catenane 41 (step 22: ref. ; steps 23–37: ref , …”

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

“…The catenane N , O ‐diacetyl‐ 36 from step 21 of Scheme (formula only shown in Scheme ) was elaborated further by Schill and his co‐workers Logemann, Vetter (in part), and Zürcher (in part) as detailed in Scheme , and the accompanying paragraphs , . Their objective was to deprive this catenane of most of the “structural extras” which let it look different than the simplest possible catenane with identical ring‐sizes.…”

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

“…)‐appendage to the 28‐membered ring of the desired final structure 41 and thereby lead to an inseparable catenane mixture. Eventually, it was found that ozonolysis cleaved off the “upper C 3 ‐moiety” of the catenane N ‐acetyl‐ 36 chemoselectively if it was performed in the presence of tetracyanoethylene , …”

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%

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

“…Conversion of catenane N , O ‐diacetyl‐ 36 (synthesis: Scheme ) into catenane 41 (step 22: ref. ; steps 23–37: ref , …”

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

Section: Catenanes From Freiburg and A Rotaxane → Catenane Conversionmentioning

confidence: 99%

See 3 more Smart Citations

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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Carbon-13 T1 measurements of medium and large ring cycloalkanes and a catenane

Fritz

Hug

Sauter

et al. 1976

Journal of Magnetic Resonance (1969)

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Polymeric Supports in General Organic Chemistry

Mathur

Narang

1980

Polymers as Aids in Organic Chemistry

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Aliphatic 1,2,3‐Triketones by Ozonolysis of Dialkyl‐1,4‐benzoquinones

Cited by 4 publications

References 6 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

Carbon-13 T1 measurements of medium and large ring cycloalkanes and a catenane

Polymeric Supports in General Organic Chemistry

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