Aziridine strategy for stereospecific synthesis of 1′-alkyl/aryl-5′-aryl-2′,5′-dihydropyrrolofullerene-2′-carboxylates and NMR study of hindered 5′-aryl group rotation

Standard

Aziridine strategy for stereospecific synthesis of 1′-alkyl/aryl-5′-aryl-2′,5′-dihydropyrrolofullerene-2′-carboxylates and NMR study of hindered 5′-aryl group rotation. / Androsov, Dmitriy V.; Konev, Alexander S.; Khlebnikov, Alexander F.

In: Tetrahedron, Vol. 111, 132734, 09.04.2022.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{fb043df870a049f4969e56914d5180fd,

title = "Aziridine strategy for stereospecific synthesis of 1′-alkyl/aryl-5′-aryl-2′,5′-dihydropyrrolofullerene-2′-carboxylates and NMR study of hindered 5′-aryl group rotation",

abstract = "A reaction of aziridines with fullerene C60 is shown to provide a stereospecific route to fulleropyrrolidines for a diverse range of substituents. The important limitation of the approach is shown to be the synthesis of N-unsubstituted fulleropyrrolidines, where the imine route described elsewhere suits better. For 2-arylsubstituted fulleropyrrolidines the activation free Gibbs energy, enthalpy and entropy of a hindered aryl group rotation are determined based on the line-shape analysis of temperature dependent NMR spectra. ortho-Fluorophenyl substituted pyrrolofullerenes are shown to have the activation barrier of ca. 16 kcal/mol, which poses these compounds as possible hindered rotors in molecular machines application.",

author = "Androsov, {Dmitriy V.} and Konev, {Alexander S.} and Khlebnikov, {Alexander F.}",

note = "Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = apr,

day = "9",

doi = "10.1016/j.tet.2022.132734",

language = "English",

volume = "111",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Aziridine strategy for stereospecific synthesis of 1′-alkyl/aryl-5′-aryl-2′,5′-dihydropyrrolofullerene-2′-carboxylates and NMR study of hindered 5′-aryl group rotation

AU - Androsov, Dmitriy V.

AU - Konev, Alexander S.

AU - Khlebnikov, Alexander F.

PY - 2022/4/9

Y1 - 2022/4/9

N2 - A reaction of aziridines with fullerene C60 is shown to provide a stereospecific route to fulleropyrrolidines for a diverse range of substituents. The important limitation of the approach is shown to be the synthesis of N-unsubstituted fulleropyrrolidines, where the imine route described elsewhere suits better. For 2-arylsubstituted fulleropyrrolidines the activation free Gibbs energy, enthalpy and entropy of a hindered aryl group rotation are determined based on the line-shape analysis of temperature dependent NMR spectra. ortho-Fluorophenyl substituted pyrrolofullerenes are shown to have the activation barrier of ca. 16 kcal/mol, which poses these compounds as possible hindered rotors in molecular machines application.

AB - A reaction of aziridines with fullerene C60 is shown to provide a stereospecific route to fulleropyrrolidines for a diverse range of substituents. The important limitation of the approach is shown to be the synthesis of N-unsubstituted fulleropyrrolidines, where the imine route described elsewhere suits better. For 2-arylsubstituted fulleropyrrolidines the activation free Gibbs energy, enthalpy and entropy of a hindered aryl group rotation are determined based on the line-shape analysis of temperature dependent NMR spectra. ortho-Fluorophenyl substituted pyrrolofullerenes are shown to have the activation barrier of ca. 16 kcal/mol, which poses these compounds as possible hindered rotors in molecular machines application.

UR - http://www.scopus.com/inward/record.url?scp=85126510223&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2022.132734

DO - 10.1016/j.tet.2022.132734

M3 - Article

AN - SCOPUS:85126510223

VL - 111

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

M1 - 132734

ER -

ID: 94086240