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https://hdl.handle.net/2440/47269
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Type: | Journal article |
Title: | On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones |
Author: | Lister, T. Prager, R. Tsaconas, M. Wilkinson, K. |
Citation: | Australian Journal of Chemistry: an international journal for chemical science, 2003; 56(9):913-916 |
Publisher: | C S I R O Publishing |
Issue Date: | 2003 |
ISSN: | 0004-9425 |
Abstract: | Analogues of 2-methoxypyridine undergo rearrangement to N-methylpyridones under flash vacuum pyrolysis (FVP) conditions. Ethoxy derivatives undergo competitive ethyl migration and elimination of ethylene. Analogues of 4-methoxypyridine do not undergo rearrangement under FVP conditions, but demethylation on silica may occur. The ease of rearrangement follows the basicity of the alkoxyhetarene to some extent. The vapour-phase rearrangements have been contrasted to condensed-phase pyrolyses, and a four-centre transition state for the former is supported by computation. The rearrangement allows structural assignment to the two products from the reaction of 2,4-dichloroquinoline with pyrrolidine. |
DOI: | 10.1071/CH03044 |
Published version: | http://www.publish.csiro.au/nid/51/paper/CH03044.htm |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 6 |
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