TY - JOUR

T1 - CYCLIC VINYL ETHERS AS THE PRODUCTS OF CYCLISATION OF 2,5,5-TRIETHYL-2-ALKYNYL-3,4-BIS(HYDROXYMETHYL)PYRROLIDINE-1-OXYLS

AU - M.m., Gulman

AU - S.a., Dobrynin

AU - Yu.v., Gatilov

AU - I.a., Kirilyuk

N1 - The work was carried out with support from the Russian Science Foundation within Project No. 23-13-00178.

PY - 2024/8/31

Y1 - 2024/8/31

N2 - 2,5,5-Triethyl-2-alkynyl-3,4-bis(hydroxymethyl)pyrrolidine-1-oxyls (alkynyl = C equivalent to CR, and R = H (2), C(Me)2OH (1), Ph (7)) undergo cyclisation on heating with sodium hydroxide to form cyclic vinyl ethers, the derivatives of 6-methylene-hexahydro-1H-furo[3,4-b]pyrrole-1-oxyl. A bicyclic radical derived from radicals 1 or 2 is capable of reversible addition of alcohols to the vinyl group in the presence of acids. Cyclisation of radical 7 in the acid environment in the presence of mercury acetate follows a different route, with the formation of 2,2,7a-triethyl3-(hydroxymethyl)-6-phenyl-1,2,3,3a,4,7a-hexahydropyrano[4,3-b]pyrrole-1-oxyl.

AB - 2,5,5-Triethyl-2-alkynyl-3,4-bis(hydroxymethyl)pyrrolidine-1-oxyls (alkynyl = C equivalent to CR, and R = H (2), C(Me)2OH (1), Ph (7)) undergo cyclisation on heating with sodium hydroxide to form cyclic vinyl ethers, the derivatives of 6-methylene-hexahydro-1H-furo[3,4-b]pyrrole-1-oxyl. A bicyclic radical derived from radicals 1 or 2 is capable of reversible addition of alcohols to the vinyl group in the presence of acids. Cyclisation of radical 7 in the acid environment in the presence of mercury acetate follows a different route, with the formation of 2,2,7a-triethyl3-(hydroxymethyl)-6-phenyl-1,2,3,3a,4,7a-hexahydropyrano[4,3-b]pyrrole-1-oxyl.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001358133800001

U2 - 10.15372/CSD2024578

DO - 10.15372/CSD2024578

M3 - Article

VL - 32

SP - 460

EP - 466

JO - Chemistry for Sustainable Development

JF - Chemistry for Sustainable Development

SN - 1817-1818

IS - 4

ER -