Reactivity of frustrated Lewis pairs with BOC protected diazocarboxylates : FLP capture of diazene
Reactions of (tBuO2CN)2 with FLPs are examined. B(C6F5)3 interacts with the carbonyl oxygen atoms inducing loss of CH2CMe2; however, in the presence of basic donors, the protons are intercepted affording the salts [Hbase]2 [((C6F5)3BO2CN)2] (base = tBu3P 1, NC5H2Ph32, HNC5H6Me43). In contrast, in the presence of (o-Tol)3P, a proton transfers to the diazo-N atom affording (o-Tol)3PN(CO2tBu)NHB(C6F5)34. Further addition of B(C6F5)3 to 4 prompts loss of olefin CH2CMe2 and CO2 affording (o-Tol)3PNHNHB(C6F5)35. The course of these reactions is examined by extensive DFT calculations. The nature of 5 is consistent with the FLP reduction of a diazene fragment.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:59 |
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| Enthalten in: |
Chemical communications (Cambridge, England) - 59(2023), 41 vom: 18. Mai, Seite 6191-6194 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Hussain, Zahid [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 21.05.2023 Date Revised 21.05.2023 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d3cc01571h |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM355968622 |
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| 100 | 1 | |a Hussain, Zahid |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Reactivity of frustrated Lewis pairs with BOC protected diazocarboxylates |b FLP capture of diazene |
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| 500 | |a Date Completed 21.05.2023 | ||
| 500 | |a Date Revised 21.05.2023 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Reactions of (tBuO2CN)2 with FLPs are examined. B(C6F5)3 interacts with the carbonyl oxygen atoms inducing loss of CH2CMe2; however, in the presence of basic donors, the protons are intercepted affording the salts [Hbase]2 [((C6F5)3BO2CN)2] (base = tBu3P 1, NC5H2Ph32, HNC5H6Me43). In contrast, in the presence of (o-Tol)3P, a proton transfers to the diazo-N atom affording (o-Tol)3PN(CO2tBu)NHB(C6F5)34. Further addition of B(C6F5)3 to 4 prompts loss of olefin CH2CMe2 and CO2 affording (o-Tol)3PNHNHB(C6F5)35. The course of these reactions is examined by extensive DFT calculations. The nature of 5 is consistent with the FLP reduction of a diazene fragment | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Luo, Yong-An |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Yile |e verfasserin |4 aut | |
| 700 | 1 | |a Qu, Zheng-Wang |e verfasserin |4 aut | |
| 700 | 1 | |a Grimme, Stefan |e verfasserin |4 aut | |
| 700 | 1 | |a Stephan, Douglas W |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemical communications (Cambridge, England) |d 1998 |g 59(2023), 41 vom: 18. Mai, Seite 6191-6194 |w (DE-627)NLM095512322 |x 1364-548X |7 nnns |
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