Cover Image

Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] Photocyclizations

Vinylogous Nazarov-type cyclizations yield seven-membered rings from butadienyl vinyl ketones via a photochemical [6π] photocyclization followed by subsequent isomerization steps. The mechanism of this recently developed method was investigated using unrestricted DFT, SF-TDDFT, and CASSCF/NEVPT2 cal...

Full description

Saved in:
Bibliographic Details
Main Authors: Pusch, Stefan (Author) , Lefrancois, Daniel (Author) , Dreuw, Andreas (Author)
Format: Article (Journal)
Language:English
Published: 2018
In: The journal of organic chemistry
Year: 2017, Volume: 83, Issue: 2, Pages: 964-972
ISSN:1520-6904
DOI:10.1021/acs.joc.7b02982
Online Access:Verlag, Volltext: https://doi.org/10.1021/acs.joc.7b02982
Verlag: https://doi.org/10.1021/acs.joc.7b02982
Get full text
Author Notes:Stefan Pusch, Andreas Tröster, Daniel Lefrancois, Pooria Farahani, Andreas Dreuw, Thorsten Bach, and Till Opatz

MARC

LEADER 00000caa a2200000 c 4500
001 1698357176
003 DE-627
005 20230427073149.0
007 cr uuu---uuuuu
008 200515r20182017xx |||||o 00| ||eng c
024 7 |a 10.1021/acs.joc.7b02982  |2 doi 
035 |a (DE-627)1698357176 
035 |a (DE-599)KXP1698357176 
035 |a (OCoLC)1341325611 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 27  |2 sdnb 
100 1 |a Pusch, Stefan  |d 1962-  |e VerfasserIn  |0 (DE-588)17267302X  |0 (DE-627)697606236  |0 (DE-576)133531341  |4 aut 
245 1 0 |a Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] Photocyclizations  |c Stefan Pusch, Andreas Tröster, Daniel Lefrancois, Pooria Farahani, Andreas Dreuw, Thorsten Bach, and Till Opatz 
246 3 3 |a Mechanism and cis / trans Selectivity of Vinylogous Nazarov-type [6pi] Photocyclizations 
264 1 |c 2018 
300 |a 9 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Published: December 22, 2017 
500 |a Gesehen am 15.05.2020 
520 |a Vinylogous Nazarov-type cyclizations yield seven-membered rings from butadienyl vinyl ketones via a photochemical [6π] photocyclization followed by subsequent isomerization steps. The mechanism of this recently developed method was investigated using unrestricted DFT, SF-TDDFT, and CASSCF/NEVPT2 calculations, suggesting three different pathways that lead either to pure trans, pure cis, or mixed cis/trans configured products. Singlet biradicals or zwitterions occur as intermediates. The computational results are supported by deuterium-labeling experiments. 
534 |c 2017 
700 1 |a Lefrancois, Daniel  |e VerfasserIn  |0 (DE-588)1147319227  |0 (DE-627)1006051287  |0 (DE-576)495813842  |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 
773 0 8 |i Enthalten in  |t The journal of organic chemistry  |d [Erscheinungsort nicht ermittelbar] : American Chemical Society, 1936  |g 83(2018), 2, Seite 964-972  |h Online-Ressource  |w (DE-627)268133387  |w (DE-600)1472273-2  |w (DE-576)090854292  |x 1520-6904  |7 nnas  |a Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] Photocyclizations 
773 1 8 |g volume:83  |g year:2018  |g number:2  |g pages:964-972  |g extent:9  |a Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] Photocyclizations 
856 4 0 |u https://doi.org/10.1021/acs.joc.7b02982  |x Verlag  |x Resolving-System  |3 Volltext 
856 4 0 |u https://doi.org/10.1021/acs.joc.7b02982  |x Verlag 
951 |a AR 
992 |a 20200515 
993 |a Article 
994 |a 2018 
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 5 
998 |g 1147319227  |a Lefrancois, Daniel  |m 1147319227:Lefrancois, Daniel  |d 700000  |d 708000  |e 700000PL1147319227  |e 708000PL1147319227  |k 0/700000/  |k 1/700000/708000/  |p 3 
999 |a KXP-PPN1698357176  |e 3667494467 
BIB |a Y 
SER |a journal 
JSO |a {"titleAlt":[{"title":"Mechanism and cis / trans Selectivity of Vinylogous Nazarov-type [6pi] Photocyclizations"}],"type":{"bibl":"article-journal","media":"Online-Ressource"},"note":["Published: December 22, 2017","Gesehen am 15.05.2020"],"language":["eng"],"relHost":[{"origin":[{"publisherPlace":"[Erscheinungsort nicht ermittelbar]","dateIssuedKey":"1936","dateIssuedDisp":"1936-","publisher":"American Chemical Society"}],"physDesc":[{"extent":"Online-Ressource"}],"id":{"zdb":["1472273-2"],"issn":["1520-6904"],"eki":["268133387"]},"title":[{"subtitle":"web edition","title":"The journal of organic chemistry","title_sort":"journal of organic chemistry"}],"recId":"268133387","corporate":[{"role":"isb","display":"American Chemical Society"}],"disp":"Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] PhotocyclizationsThe journal of organic chemistry","type":{"bibl":"periodical","media":"Online-Ressource"},"pubHistory":["1.1936/37 -"],"note":["Gesehen am 25.08.2020"],"part":{"volume":"83","year":"2018","pages":"964-972","extent":"9","issue":"2","text":"83(2018), 2, Seite 964-972"},"language":["eng"]}],"origin":[{"dateIssuedKey":"2018","dateIssuedDisp":"2018"}],"title":[{"title":"Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] Photocyclizations","title_sort":"Mechanism and cis/trans Selectivity of Vinylogous Nazarov-type [6π] Photocyclizations"}],"id":{"doi":["10.1021/acs.joc.7b02982"],"eki":["1698357176"]},"physDesc":[{"extent":"9 S."}],"person":[{"family":"Pusch","role":"aut","display":"Pusch, Stefan","given":"Stefan"},{"family":"Lefrancois","role":"aut","display":"Lefrancois, Daniel","given":"Daniel"},{"role":"aut","family":"Dreuw","given":"Andreas","display":"Dreuw, Andreas"}],"recId":"1698357176","name":{"displayForm":["Stefan Pusch, Andreas Tröster, Daniel Lefrancois, Pooria Farahani, Andreas Dreuw, Thorsten Bach, and Till Opatz"]}} 
SRT |a PUSCHSTEFAMECHANISMA2018 

Similar Items