Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/32694
Title: Hetero-diels-alder reaction of ethyl 2-nitrosoacrylate and cyclohexadienes, and bromine induced diene isomerization
Authors: Song, J
Lin, Y
Szeto, YS 
Chan, WL
Issue Date: 2006
Source: Heterocycles, 2006, v. 68, no. 8, p. 1685-1689 How to cite?
Journal: Heterocycles 
Abstract: Bicyclic 8a-methoxy-1,2-oxazine (3a) and bicyclic 7-methoxy-1,2-oxazine (3b) were prepared via Hetero-Diels-Alder reaction between 1-methoxy-1,4-cyclohexadiene (2a) and ethyl 2-nitrosoacrylate generated in situ from ethyl bromopyruvate oxime (1). The formation of 3b was ascribed to bromine, released from 1, which induced transformation of 2a to 1-methoxy-1,3-cyclohexadiene (2b). 3b could be easily transformed to oxazinone (3c) in CHCl 3, or other organic solvents in the presence of a trace amount of acid.{A figure is presented}.
URI: http://hdl.handle.net/10397/32694
ISSN: 0385-5414
DOI: 10.3987/COM-06-10737
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