American Chemical Society (ACS)
Organic Letters
,  volume 21 ,  issue 13 ,  pages 5162-5166

Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction

Publication type: Journal Article
Publication date: 2019-06-14
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Three Prato monoadduct isomers were synthesized and structurally characterized by 1H, 13C NMR spectra and single-crystal X-ray diffraction, and one adduct on the dd-[5,6]-bond was found as the first example of a Prato [5,6]-adduct of C70. To investigate the mechanism in the generation of this dd-[5,6]-adduct, computational studies were employed to show that it was thermodynamically obtained by sigmatropic rearrangement from the presumed initial kinetic product de-[6,6]-adduct.
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GOST Copy
Liosi K. et al. Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction // Organic Letters. 2019. Vol. 21. No. 13. pp. 5162-5166.
GOST all authors (up to 50) Copy
Liosi K., Romero Rivera A., Semivrazhskaya O., Caniglia C. D., Garcia-Borràs M., Kassiou M., Osuna S., Yamakoshi Y. Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction // Organic Letters. 2019. Vol. 21. No. 13. pp. 5162-5166.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.9b01756
UR - https://doi.org/10.1021/acs.orglett.9b01756
TI - Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction
T2 - Organic Letters
AU - Liosi, Korinne
AU - Romero Rivera, Adrian
AU - Semivrazhskaya, Olesya
AU - Caniglia, Caravaggio D
AU - Garcia-Borràs, Marc
AU - Kassiou, M.
AU - Osuna, Sílvia
AU - Yamakoshi, Yoko
PY - 2019
DA - 2019/06/14
PB - American Chemical Society (ACS)
SP - 5162-5166
IS - 13
VL - 21
PMID - 31199152
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Liosi,
author = {Korinne Liosi and Adrian Romero Rivera and Olesya Semivrazhskaya and Caravaggio D Caniglia and Marc Garcia-Borràs and M. Kassiou and Sílvia Osuna and Yoko Yamakoshi},
title = {Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.9b01756},
number = {13},
pages = {5162--5166},
doi = {10.1021/acs.orglett.9b01756}
}
MLA
Cite this
MLA Copy
Liosi, Korinne, et al. “Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction.” Organic Letters, vol. 21, no. 13, Jun. 2019, pp. 5162-5166. https://doi.org/10.1021/acs.orglett.9b01756.