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200517.fm Page 186 Friday, March 18, 2005 2:52 PM
2005
Oxazine derivatives
R 0595
New C—C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles.
of the Conventional Reactivity of Nitronates. — In the presence of
17- 167 Umpolung
TbsOTf cyclic nitronates such as (I), (IV), (VI), and (VIII) are found to undergo successful reaction with nucleophiles to afford C-3 functionalized tetrahydrooxazines.
This indicates that nitronates also possess electrophilic activity. — (SMIRNOV, V. O.;
IOFFE*, S. L.; TISHKOV, A. A.; KHOMUTOVA, Y. A.; NESTEROV, I. D.;
ANTIPIN, M. Y.; SMIT, W. A.; TARTAKOVSKY, V. A.; J. Org. Chem. 69 (2004) 24,
8485-8488; Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia;
Eng.) — Jannicke
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