Observation of a Thermally Induced Bora-Nazarov Cyclization at a Phosphole Framework
The reaction of the bis(enynyl)phosphanes 6 a,b with the electrophilic borane reagents RB(C6F5)2 (R=C6F5, CH2CH2Ph, CH3) gave phospholes cleanly in a 1,1‐carboboration reaction sequence. Depending on the steric bulk, the resulting 2,5‐alkenylphospholes underwent a thermally induced bora‐Nazarov typ...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-10, Vol.54 (42), p.12366-12369 |
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| container_issue | 42 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Möbus, Juri Kehr, Gerald Daniliuc, Constantin G. Mück-Lichtenfeld, Christian Erker, Gerhard |
| description | The reaction of the bis(enynyl)phosphanes 6 a,b with the electrophilic borane reagents RB(C6F5)2 (R=C6F5, CH2CH2Ph, CH3) gave phospholes cleanly in a 1,1‐carboboration reaction sequence. Depending on the steric bulk, the resulting 2,5‐alkenylphospholes underwent a thermally induced bora‐Nazarov type cyclization. The equilibrium situation of these examples of a bora‐Nazarov type cyclization was investigated in detail by NMR spectroscopy, X‐ray crystal structure analysis, and DFT calculations.
Ringing the changes: 2,5‐Alkenyl‐substituted phospholes bearing an adjacent electrophilic borane can undergo a thermally induced bora‐Nazarov type ring closure. Tipp=2,4,6‐triisopropylphenyl. |
| doi_str_mv | 10.1002/anie.201502850 |
| format | Article |
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| subjects | 1,1‐carboboration reactions 1-carboboration reactions Bearing bora-Nazarov reaction Boranes Cleaning Closures conjugated π-systems Crystal structure cyclization Mathematical analysis NMR spectroscopy phospholes X-rays |
| title | Observation of a Thermally Induced Bora-Nazarov Cyclization at a Phosphole Framework |
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