Macrocyclic Systems Containing 2,6,9-Trioxabicyclo[3.3.1]-nona-3,7-dienes as Chiral Spacer Groups: Synthesis, Stereochemical Features and Preliminary Complexation Properties

Чебанов, Валентин А.; Reidlinger, Claudia; Kanaani, Hussein; Wentrup, Curt; Kappe, C. Oliver; Kollenz, G.

doi:10.1080/10610270310001614197

Cited by 16 publications

(13 citation statements)

References 19 publications

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“…Scheme 42. Aziridine [203] and cyclopropane ring-opening, [204] double Michael addition, [205] lactam formation, [206] and reduction of a nitro group by catalytic transfer hydrogenation. [207] Ts = toluenesulfonyl.…”

Section: 9mentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: 9mentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“… Aziridin‐203 und Cyclopropan‐Ringöffnung,204 doppelte Michael‐Addition,205 Lactambildung206 und Reduktion einer Nitrogruppe durch katalytische Transferhydrogenierung 207. Ts=Toluolsulfonyl.…”

Section: Literaturüberblickunclassified

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

Kappe

2004

Angewandte Chemie

246

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Die offene Flamme konnte erst gezielt als Heizquelle für Reaktionsgefäße in der Synthesechemie verwendet werden, nachdem Robert Bunsen 1855 den nach ihm benannten Brenner erfunden hatte. Der Bunsen‐Brenner wurde später durch den Heizpilz, das Ölbad und die Heizplatte als Wärmequellen für chemische Reaktionen abgelöst. In den vergangenen Jahren ist das Erhitzen und Beschleunigen chemischer Reaktionen durch Mikrowellenenergie populär geworden. Diese Heiztechnik hat sich von einer Laborkuriosität zu einer etablierten Methode entwickelt, die an Universitäten und in der Industrie stark genutzt wird. Die effiziente Verringerung der Reaktionszeiten (von Tagen und Stunden auf Minuten und Sekunden) ist nur einer der vielen Vorteile des schnellen Erhitzens mit Mikrowellen (“microwave flash heating”). Dieser Aufsatz gibt einen Überblick über neuere Anwendungen des kontrollierten Mikrowellenerhitzens in der modernen organischen Synthese und diskutiert einige grundlegende Vorgänge.

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“…Moreover, Chebanov et al. have reported that macrocyclic compounds were also obtained by reacting bisacid dichlorides with diol and dithia octanediol . Therefore, we tried to obtain the desired polymer by thiol‐Michael addition.…”

Section: Resultsmentioning

confidence: 92%

“…Unfortunately, only low molecular weight oligomers (<1000 g⋅mol −1 ) were obtained. This phenomenon was attributed to the formation of a mixture of oligomers and macrocycles instead of long linear polymers as previously reported by some research groups . Indeed, diacyls containing heteroatoms (oxygen, or sulfur) in their chemical structure produced macrocycles through condensation with diols.…”

Section: Resultsmentioning

confidence: 99%

Oligo(thioether‐ester)s Blocks in Polyurethanes for Slowly Releasing Active Payloads

Klahan

Seidi

Crespy

2018

Macro Chemistry & Physics

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The preparation of acid‐responsive degradable oligomers with active agents in their main chains is described. Dichlorophene (DCP), an effective anticestodal agent, and the corrosion inhibitor 4‐(2‐pyridylazo)resorcinol (PAR) are reacted to form polymerizable bisacrylate derivatives. The derivatives are then copolymerized with aliphatic and aromatic dithiols by thiol‐Michael addition to obtain a polymer backbone with cleavable thiopropionate groups. Low molecular weight (M n < 10 000 g mol−1) linear oligomers are obtained, which can be used for the preparation of poly(ester‐urethane)s. Polymer nanoparticles from both oligo(thioether‐ester) and poly(ester‐urethane)s are fabricated by the miniemulsion‐solvent evaporation method. The polymers in solution and dispersion can be gradually degraded in acidic media. The degraded products of the degradation of PAR containing polymers can be detected in the presence of copper ions.

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Macrocyclic Systems Containing 2,6,9-Trioxabicyclo[3.3.1]-nona-3,7-dienes as Chiral Spacer Groups: Synthesis, Stereochemical Features and Preliminary Complexation Properties

Cited by 16 publications

References 19 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

Oligo(thioether‐ester)s Blocks in Polyurethanes for Slowly Releasing Active Payloads

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