Selenium- and tellurium-substituted cyclopropenones and their facile ring-opening with methanol
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 cha...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2003
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| In: |
European journal of organic chemistry
Year: 2002, Issue: 1, Pages: 151-154 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200301)2003:1<151::AID-EJOC151>3.0.CO;2-7 |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/1099-0690(200301)2003:1<151::AID-EJOC151>3.0.CO;2-7 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200301%292003%3A1%3C151%3A%3AAID-EJOC151%3E3.0.CO%3B2-7 
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| Author Notes: | Daniel B. Werz, Rolf Gleiter, and Frank Rominger |
| Summary: | 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) |
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| Item Description: | First published: 05 December 2002 Gesehen am 27.10.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200301)2003:1<151::AID-EJOC151>3.0.CO;2-7 |