@article{2f3dd31f9e6a41eeba41eeedfc08d7ac,
title = "Unexpected one-pot formation of the 1H-6a,8a-epiminotri-cyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study",
abstract = "The unexpected formation of a highly strained polycyclic amine was observed in a one-pot synthesis from cyclopentanone, dimethyl fumarate and ammonium acetate. This multistep reaction includes 1,3-dipolar cycloaddition of dimethyl fumarate to the cyclic azomethine ylide formed in situ from cyclopentanone and ammonia. The polycyclic amine product was easily converted into a sterically shielded polycyclic nitroxide. The EPR spectra and spin relaxation behavior of the nitroxide were studied in solution. The spin relaxation seems well suited for the use as a biological spin label and are comparable with those of cyclic nitroxides with two spirocyclic moieties adjacent to the N–O· group.",
keywords = "Domino reactions, EPR, Nitroxide, Spin relaxation, DISTANCE MEASUREMENTS, RELAXATION RATES, PROTEIN, domino reactions, spin relaxation, nitroxide, RADICALS, SPIN-LABEL",
author = "Dobrynin, {Sergey A.} and Kirilyuk, {Igor A.} and Gatilov, {Yuri V.} and Kuzhelev, {Andrey A.} and Krumkacheva, {Olesya A.} and Fedin, {Matvey V.} and Bowman, {Michael K.} and Bagryanskaya, {Elena G.}",
note = "Copyright {\textcopyright} 2019, Dobrynin et al.; licensee Beilstein-Institut.",
year = "2019",
month = nov,
day = "7",
doi = "10.3762/bjoc.15.259",
language = "English",
volume = "15",
pages = "2664--2670",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",
}