Evidence for an intramolecular elimination mechanism in the aqueous decomposition of ( N-Cl)-alcoholamines

• Published in: Tetrahedron Vol. 53; no. 7; pp. 2565 - 2572
• Main Authors: Armesto, X.L., Canle L., M., Carretero, P., García, M.V., Santaballa, J.A.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 17.02.1997
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(96)01145-3

(N-Cl)-alcoholamines decompose in aqueous medium through two main reaction paths: an intramolecular elimination and a fragmentation. Both mechanisms take place following a pre-equilibrium deprotonation of the β-hydroxyl group of the (N-Cl)-compound. Evidences for both pathways are given and a very high effective molarity (EM=0.2·10 6 M) is reported for the intramolecular process. ( N-Cl)-alcoholamines decompose by two main reaction paths: an intramolecular elimination and a fragmentation. Both take place following a pre-equilibrium deprotonation of the -OH of the ( N-Cl)-compound. Evidences for this are given and a very high effective molarity is reported for the intramolecular process.