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Elsevier, Tetrahedron Letters, 3(43), p. 481-485

DOI: 10.1016/s0040-4039(01)02150-5

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Novel rearrangement of secondary alkoxyalkyl radicals during addition to a double bond. Steric shielding in the formation of tertiary alkoxyethyl radicals

Journal article published in 2002 by Oldřich Paleta, Jan Hajduch ORCID, Stanislav Bőhm
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The participation of a 1,3-hydrogen shift in initially formed secondary alkoxyethyl radicals R1R2CH-O-CH-CH3 during their free-radical chain additions to methyl 2,3,3-trifluoroacrylate has been confirmed using a deuterium marked additive. Indirect evidence has been obtained for a partial 1,3-hydrogen shift in secondary radicals CH3(CH2)n-CH-O-CH3 to primary radicals CH3(CH2)n-CH2-O-CH2. Initial formation of tertiary alkoxyethyl radicals R1R2C-O-CHR3R4 in the propagation step was not observed due to steric factors.