Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes

Bulman Page, Philip C., Heaney, Harry, McGrath, Matthew J., Sampler, Edward P. and Wilkins, Robert F. (2003) Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes. Tetrahedron Letters, 44 (14). pp. 2965-2970. ISSN 0040-4039

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Abstract

Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: solvent,resorcinarenes,generation,derivatives,o-quinone methide,axially chiral,heterocycles,o-quinone methides,reactivity,aminol ethers
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 09:55
Last Modified: 10 Jun 2020 23:47
URI: https://ueaeprints.uea.ac.uk/id/eprint/32847
DOI: 10.1016/s0040-4039(03)00393-9

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