Selenium- and tellurium-substituted cyclopropenones and their facile ring-opening with methanol

• Verfasst von: Werz, Daniel B. [VerfasserIn]
• Verfasst von: Gleiter, Rolf [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Titel: Selenium- and tellurium-substituted cyclopropenones and their facile ring-opening with methanol
• Verf.angabe: Daniel B. Werz, Rolf Gleiter, and Frank Rominger
• Jahr: 2003
• Jahr des Originals: 2002
• Umfang: 4 S.
• Teil: year:2003
• Teil: number:1
• Teil: pages:151-154
• Teil: extent:4
• Fussnoten: First published: 05 December 2002 ; Gesehen am 27.10.2020
• Titel Quelle: Enthalten in: European journal of organic chemistry
• Ort Quelle: Weinheim : Wiley-VCH Verl., 1998
• Jahr Quelle: 2003
• Band/Heft Quelle: (2003), 1, Seite 151-154
• ISSN Quelle: 1099-0690
• DOI: doi:10.1002/1099-0690(200301)2003:1<151::AID-EJOC151>3.0.CO;2-7
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Cyclopropenones
• Sach-SW: DFT calculations
• Sach-SW: Selenium
• Sach-SW: Tellurium
• K10plus-PPN: 1736675621

Abstract

Treatment of donor-substituted acetylenes (X−C≡C−X, with X = R−Se, R−Te) with sodium trichloroacetate, followed by hydrolysis, yielded the corresponding cyclopropenones. Their structures could be elucidated by X-ray analysis, and indicated significant overlap between the p-type lone pairs on the chalcogen atoms and the cyclopropenone unit. DFT calculations were carried out on various conformers in order to clarify their relative energy profiles. Methanolysis of these ring systems at room temperature quantitatively afforded α,β-unsaturated esters. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)