dc.identifier.uri |
http://dx.doi.org/10.15488/14960 |
|
dc.identifier.uri |
https://www.repo.uni-hannover.de/handle/123456789/15079 |
|
dc.contributor.author |
Boston, Geanne M. R.
|
|
dc.contributor.author |
Frank, Irmgard
|
|
dc.contributor.author |
Butenschön, Holger
|
|
dc.date.accessioned |
2023-10-16T07:34:27Z |
|
dc.date.available |
2023-10-16T07:34:27Z |
|
dc.date.issued |
2021 |
|
dc.identifier.citation |
Boston, G.M.R.; Frank, I.; Butenschön, H.: Anionic Thia-Fries Rearrangement at Ferrocene: A Computational and Experimental Study. In: Helvetica Chimica Acta 104 (2021), Nr. 4, e2100025. DOI: https://doi.org/10.1002/hlca.202100025 |
|
dc.description.abstract |
Ferrocenyl triflate (1) and 1,1′-ferrocenediyl ditriflate (5) undergo single and double anionic thia-Fries rearrangements at low temperatures in high yields with the latter forming exclusively the respective meso product. The detailed mechanisms of the anionic thia-Fries rearrangement of 1, as well as that of the double anionic thia-Fries rearrangement of 5, are examined with the aid of DFT calculations. Functionals, basis set and pseudopotentials applied were selected in accordance with a benchmark using the crystal structure analysis of the prime product 3 of the reaction of 1 before hydrolysis for comparison, which has so far not been reported. The unprecedented meso diastereoselectivity of the double anionic thia-Fries rearrangement of 5 is shown to be a result of a distinctive degree of chelation arising from two diastereomeric transition states. |
eng |
dc.language.iso |
eng |
|
dc.publisher |
New York, NY : Wiley-VCH |
|
dc.relation.ispartofseries |
Helvetica Chimica Acta 104 (2021), Nr. 4 |
|
dc.rights |
CC BY 4.0 Unported |
|
dc.rights.uri |
https://creativecommons.org/licenses/by/4.0 |
|
dc.subject |
anionic thia-Fries rearrangement |
eng |
dc.subject |
crystal structure analysis |
eng |
dc.subject |
density functional calculations |
eng |
dc.subject |
ferrocenyl triflates |
eng |
dc.subject |
reaction mechanisms |
eng |
dc.subject.ddc |
540 | Chemie
|
|
dc.title |
Anionic Thia-Fries Rearrangement at Ferrocene: A Computational and Experimental Study |
eng |
dc.type |
Article |
|
dc.type |
Text |
|
dc.relation.essn |
1522-2675 |
|
dc.relation.issn |
0018-019X |
|
dc.relation.doi |
https://doi.org/10.1002/hlca.202100025 |
|
dc.bibliographicCitation.issue |
4 |
|
dc.bibliographicCitation.volume |
104 |
|
dc.bibliographicCitation.firstPage |
e2100025 |
|
dc.description.version |
publishedVersion |
eng |
tib.accessRights |
frei zug�nglich |
|
dc.bibliographicCitation.articleNumber |
e2100025 |
|