Synthesis 2006(21): 3706-3710  
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

Tatiana Klimova Berestneva*a, Elena I. Klimovaa, Marcos Flores-Alamoa, Leon V. Backinowskyb, Marcos Martínez Garcíac
a Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P. 04510, México D.F., Mexico
Fax: +52(5)556225371; e-Mail: klimova@servidor.unam.mx;
b N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation
c Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P. 04510, México D.F., Mexico
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.