Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiation
Herein we disclose a systematic evaluation of the scope and limitations for the use of alkynyl triazenes for the synthesis of cyano-substituted cyclopropanes and cyclopropenes. The method is based on the formation of a cyanocarbene by cleavage of the N1-N2 bond of the alkynyl triazene precursor unde...
Gespeichert in:
| Hauptverfasser: | , , , , , , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
[30 Dec 2024]
|
| In: |
Organic chemistry frontiers
Year: 2025, Jahrgang: 12, Heft: 7, Pages: 2180-2186 |
| ISSN: | 2052-4129 |
| DOI: | 10.1039/D4QO02023E |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1039/D4QO02023E Verlag, kostenfrei, Volltext: https://pubs.rsc.org/en/content/articlelanding/2025/qo/d4qo02023e 
|
| Verfasserangaben: | Melina Maag, Linus Bjarne Dittmer, Elena Michel, Alexandra V. Mackenroth, Martin C. Dietl, Frank Rominger, Matthias Rudolph, Andreas Dreuw and A. Stephen K. Hashmi |
MARC
| LEADER | 00000naa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1932196242 | ||
| 003 | DE-627 | ||
| 005 | 20250731130311.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 250731s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1039/D4QO02023E |2 doi | |
| 035 | |a (DE-627)1932196242 | ||
| 035 | |a (DE-599)KXP1932196242 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Maag, Melina |e VerfasserIn |0 (DE-588)1344867693 |0 (DE-627)1905611196 |4 aut | |
| 245 | 1 | 0 | |a Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiation |c Melina Maag, Linus Bjarne Dittmer, Elena Michel, Alexandra V. Mackenroth, Martin C. Dietl, Frank Rominger, Matthias Rudolph, Andreas Dreuw and A. Stephen K. Hashmi |
| 264 | 1 | |c [30 Dec 2024] | |
| 300 | |a 7 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 31.07.2025 | ||
| 520 | |a Herein we disclose a systematic evaluation of the scope and limitations for the use of alkynyl triazenes for the synthesis of cyano-substituted cyclopropanes and cyclopropenes. The method is based on the formation of a cyanocarbene by cleavage of the N1-N2 bond of the alkynyl triazene precursor under UV light, which then reacts with a styrene or alkyne to form the respective products, making this a simple approach avoiding metals typically used in related reactions of organic azides. Different substituents on the triazene moiety, N-terminus and styrene/alkyne were investigated concerning their influence on the yield and diastereoselectivity with respect to the resulting cyclopropanes. The study showed that electron-rich aryl substituents at the alkynyl triazenes enable a good diastereomeric excess favouring the anti-diastereomer. Accompanying computational studies revealed that this diastereomeric preference can be qualitatively predicted from the relative stability of the singlet and triplet states of the cyanocarbene, as well as the dispersive attraction between the carbene and the olefin. | ||
| 700 | 1 | |a Dittmer, Linus Bjarne |e VerfasserIn |0 (DE-588)1328390527 |0 (DE-627)1887857958 |4 aut | |
| 700 | 1 | |a Michel, Elena |d 1994- |e VerfasserIn |0 (DE-588)1199027243 |0 (DE-627)1681397552 |4 aut | |
| 700 | 1 | |a Mackenroth, Alexandra |d 1993- |e VerfasserIn |0 (DE-588)1171260164 |0 (DE-627)1040456103 |0 (DE-576)513664025 |4 aut | |
| 700 | 1 | |a Dietl, Martin C. |d 1994- |e VerfasserIn |0 (DE-588)1165526328 |0 (DE-627)1029459606 |0 (DE-576)510403670 |4 aut | |
| 700 | 1 | |a Rominger, Frank |d 1964- |e VerfasserIn |0 (DE-588)1019978228 |0 (DE-627)691067821 |0 (DE-576)359202756 |4 aut | |
| 700 | 1 | |a Rudolph, Matthias |d 1975- |e VerfasserIn |0 (DE-588)136790380 |0 (DE-627)587252405 |0 (DE-576)301277524 |4 aut | |
| 700 | 1 | |a Dreuw, Andreas |d 1972- |e VerfasserIn |0 (DE-588)1060214598 |0 (DE-627)799305626 |0 (DE-576)416304974 |4 aut | |
| 700 | 1 | |a Hashmi, A. Stephen K. |d 1963- |e VerfasserIn |0 (DE-588)101199576X |0 (DE-627)704823926 |0 (DE-576)169176665 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic chemistry frontiers |d Cambridge : RSC, 2014 |g 12(2025), 7, Seite 2180-2186 |h Online-Ressource |w (DE-627)778443094 |w (DE-600)2757215-8 |w (DE-576)401480224 |x 2052-4129 |7 nnas |a Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiation |
| 773 | 1 | 8 | |g volume:12 |g year:2025 |g number:7 |g pages:2180-2186 |g extent:7 |a Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiation |
| 856 | 4 | 0 | |u https://doi.org/10.1039/D4QO02023E |x Verlag |x Resolving-System |z kostenfrei |3 Volltext |
| 856 | 4 | 0 | |u https://pubs.rsc.org/en/content/articlelanding/2025/qo/d4qo02023e |x Verlag |z kostenfrei |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20250731 | ||
| 993 | |a Article | ||
| 994 | |a 2024 | ||
| 998 | |g 101199576X |a Hashmi, A. Stephen K. |m 101199576X:Hashmi, A. Stephen K. |d 120000 |d 120100 |e 120000PH101199576X |e 120100PH101199576X |k 0/120000/ |k 1/120000/120100/ |p 9 |y j | ||
| 998 | |g 1060214598 |a Dreuw, Andreas |m 1060214598:Dreuw, Andreas |d 700000 |d 708000 |e 700000PD1060214598 |e 708000PD1060214598 |k 0/700000/ |k 1/700000/708000/ |p 8 | ||
| 998 | |g 136790380 |a Rudolph, Matthias |m 136790380:Rudolph, Matthias |d 120000 |d 120100 |e 120000PR136790380 |e 120100PR136790380 |k 0/120000/ |k 1/120000/120100/ |p 7 | ||
| 998 | |g 1019978228 |a Rominger, Frank |m 1019978228:Rominger, Frank |d 120000 |d 120100 |e 120000PR1019978228 |e 120100PR1019978228 |k 0/120000/ |k 1/120000/120100/ |p 6 | ||
| 998 | |g 1165526328 |a Dietl, Martin C. |m 1165526328:Dietl, Martin C. |d 120000 |d 120100 |e 120000PD1165526328 |e 120100PD1165526328 |k 0/120000/ |k 1/120000/120100/ |p 5 | ||
| 998 | |g 1171260164 |a Mackenroth, Alexandra |m 1171260164:Mackenroth, Alexandra |d 120000 |d 120100 |e 120000PM1171260164 |e 120100PM1171260164 |k 0/120000/ |k 1/120000/120100/ |p 4 | ||
| 998 | |g 1344867693 |a Maag, Melina |m 1344867693:Maag, Melina |d 120000 |d 120100 |e 120000PM1344867693 |e 120100PM1344867693 |k 0/120000/ |k 1/120000/120100/ |p 1 |x j | ||
| 999 | |a KXP-PPN1932196242 |e 4751539280 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"relHost":[{"origin":[{"publisher":"RSC","dateIssuedDisp":"2014-","dateIssuedKey":"2014","publisherPlace":"Cambridge"}],"id":{"zdb":["2757215-8"],"eki":["778443094"],"issn":["2052-4129"]},"physDesc":[{"extent":"Online-Ressource"}],"title":[{"title":"Organic chemistry frontiers","subtitle":"an international journal of organic chemistry","title_sort":"Organic chemistry frontiers"}],"recId":"778443094","disp":"Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiationOrganic chemistry frontiers","type":{"media":"Online-Ressource","bibl":"periodical"},"note":["Gesehen am 13.02.14"],"pubHistory":["1.2014 -"],"part":{"volume":"12","year":"2025","text":"12(2025), 7, Seite 2180-2186","pages":"2180-2186","extent":"7","issue":"7"},"language":["eng"]}],"origin":[{"dateIssuedKey":"2024","dateIssuedDisp":"[30 Dec 2024]"}],"title":[{"title":"Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiation","title_sort":"Scope and mechanistic insight into the chemistry of cyanocarbenes derived from alkynyl triazenes by UV irradiation"}],"type":{"bibl":"article-journal","media":"Online-Ressource"},"id":{"eki":["1932196242"],"doi":["10.1039/D4QO02023E"]},"physDesc":[{"extent":"7 S."}],"recId":"1932196242","person":[{"given":"Melina","display":"Maag, Melina","role":"aut","family":"Maag"},{"given":"Linus Bjarne","display":"Dittmer, Linus Bjarne","family":"Dittmer","role":"aut"},{"display":"Michel, Elena","given":"Elena","family":"Michel","role":"aut"},{"given":"Alexandra","display":"Mackenroth, Alexandra","family":"Mackenroth","role":"aut"},{"family":"Dietl","role":"aut","given":"Martin C.","display":"Dietl, Martin C."},{"given":"Frank","display":"Rominger, Frank","family":"Rominger","role":"aut"},{"family":"Rudolph","role":"aut","given":"Matthias","display":"Rudolph, Matthias"},{"display":"Dreuw, Andreas","given":"Andreas","family":"Dreuw","role":"aut"},{"role":"aut","family":"Hashmi","given":"A. Stephen K.","display":"Hashmi, A. Stephen K."}],"note":["Gesehen am 31.07.2025"],"language":["eng"],"name":{"displayForm":["Melina Maag, Linus Bjarne Dittmer, Elena Michel, Alexandra V. Mackenroth, Martin C. Dietl, Frank Rominger, Matthias Rudolph, Andreas Dreuw and A. Stephen K. Hashmi"]}} | ||
| SRT | |a MAAGMELINASCOPEANDME3020 | ||