Buchumschlag

Syntheses and structural properties of cyclic tetrathiadiynes

The four-component cyclization of dilithium acetylide with dithiocyanatoalkanes yielded the hitherto unknown tetrathiacyclodiynes 34, 38, 41, and 43 in moderate yields. The use of the trimethylsilyl protecting group allowed a more efficient and flexible stepwise approach with good yields. The result...

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Bibliographische Detailangaben
Hauptverfasser: Benisch, Christoph (VerfasserIn) , Bethke, Sabine (VerfasserIn) , Gleiter, Rolf (VerfasserIn) , Oeser, Thomas (VerfasserIn) , Pritzkow, Hans (VerfasserIn) , Rominger, Frank (VerfasserIn)
Dokumenttyp: Article (Journal) Festschrift
Sprache:Englisch
Veröffentlicht: 03 July 2000
In: European journal of organic chemistry
Year: 2000, Heft: 13, Pages: 2479-2488
ISSN:1099-0690
DOI:10.1002/1099-0690(200007)2000:13<2479::AID-EJOC2479>3.0.CO;2-9
Schlagworte:
Festschrift
Online-Zugang:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/1099-0690(200007)2000:13<2479::AID-EJOC2479>3.0.CO;2-9
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200007%292000%3A13%3C2479%3A%3AAID-EJOC2479%3E3.0.CO%3B2-9
Volltext
Verfasserangaben:Christoph Benisch, Sabine Bethke, Rolf Gleiter, Thomas Oeser, Hans Pritzkow, and Frank Rominger
Beschreibung
Zusammenfassung:The four-component cyclization of dilithium acetylide with dithiocyanatoalkanes yielded the hitherto unknown tetrathiacyclodiynes 34, 38, 41, and 43 in moderate yields. The use of the trimethylsilyl protecting group allowed a more efficient and flexible stepwise approach with good yields. The resulting tetrathiacyclodiynes 25−44 were investigated by X-ray analysis. For ring systems with a twist-chair conformation the torsion angle between the CH2−S σ-bonds of the CH2−S−C≡C−S−CH2 moiety adopts values between 75° and 110°. These values are due to electronic effects, as shown by HF/6-31G* calculations.
Beschreibung:Dedicated to Professor Franz Effenberger on the occasion of his 70th birthday
Gesehen am 27.10.2020
Beschreibung:Online Resource
ISSN:1099-0690
DOI:10.1002/1099-0690(200007)2000:13<2479::AID-EJOC2479>3.0.CO;2-9

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