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Synthesis 2006(21): 3706-3710
DOI: 10.1055/s-2006-950288
DOI: 10.1055/s-2006-950288
PAPER
© Georg Thieme Verlag Stuttgart · New York
Formation of 4,5-Diferrocenyl-6-(methylsulfanyl)-6H-1,2-oxazine N-Oxides and Migration of a Nitro Group in Reactions of 2,3-Diferrocenyl-1-(methylsulfanyl)cyclopropenylium Iodide with Nitroalkanes
Further Information
Publication History
Received
12 May 2006
Publication Date:
09 October 2006 (online)


Abstract
A new method of synthesis of nitrosooxy- and nitro-substituted diferrocenyl-1,3-dienes and diferrocenyl(methylsulfanyl)-6H-1,2-oxazine N-oxides by reactions of diferrocenyl(methylsulfanyl)cyclopropenylium iodide with nitroalkanes in the presence of triethylamine at 20 °C is described. This reaction is accompanied by migration of a nitro group in the transient species or intramolecular cyclization. The structure of one of the 1,2-oxazine N-oxides has been confirmed by X-ray diffraction analysis.
Key words
diferrocenyl(methylsulfanyl)cyclopropenylium - 6H-1,2-oxazine N-oxides - cyclopropene ring opening - nitro-group migration - 2,3-diferrocenyl-1-nitrobuta-1,3-dienes