Electron Spin Resonance Studies in Aqueous Solution: Fragmentation of Radical Intermediates Derived from β-Amino Alcohols

15 December 1973

journal article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 51 (24) , 4009-4017
https://doi.org/10.1139/v73-598

Abstract

In acidic aqueous solution, oxidation of the β-amino alcohols [Formula: see text], I, and [Formula: see text], II, (R = H, alkyl) using the Ti(III)–H2O2 flow technique gave the radicals [Formula: see text], and [Formula: see text]. The spectrum of [Formula: see text] shows restricted rotation about the C1—C2 bond assigned to intramolecular hydrogen bonding.Under neutral conditions, oxidation of I gave the spectrum of •CH2CHO, and of II the acetonyl radical •CH2COCH3. It is proposed that elimination occurs by deprotonation of the abstraction radical in a hydrogen-bonded conformation, followed by rapid fragmentation to yield the α-carbonyl radical.

Keywords

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