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

Sergey A. Dobrynin, Igor A. Kirilyuk, Yuri V. Gatilov, Andrey A. Kuzhelev, Olesya A. Krumkacheva, Matvey V. Fedin, Michael K. Bowman, Elena G. Bagryanskaya

Результат исследования: Научные публикации в периодических изданияхстатья

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)2664-2670
Число страниц7
ЖурналBeilstein Journal of Organic Chemistry
Том15
DOI
СостояниеОпубликовано - 7 ноя 2019

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