Unexpected one-pot formation of 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and  EPR study

Submitting author affiliation:
NIOCH SB RAS, Novosibirsk, Russian Federation

Beilstein Arch. 2019, 201987. https://doi.org/10.3762/bxiv.2019.87.v1

Published 20 Aug 2019

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The unexpected formation of a highly strained polycyclic amine was found in a one-pot synthesis from cyclopentanone, dimethylfumarate 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 was studied in solution.  The spin relaxation seems well suited for use as a biological spin label and are comparable with those of cyclic nitroxides with two spirocyclic moieties adjacent to N-O• group.

Keywords: Domino reaction, azomethine ylide, nitroxide

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Dobrynin, S.; Kirilyuk, I.; Gatilov, Y.; Kuzhelev, A.; Krumkacheva, O.; Fedin, M.; Bowman, M.; Bagryanskaya, E. Beilstein Arch. 2019, 201987. doi:10.3762/bxiv.2019.87.v1

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