alpha-organoelement nitrones: Synthesis, properties, and IR and C-13 NMR spectral and X-ray structural characterization

alpha-organoelement nitrones: Synthesis, properties, and IR and C-13 NMR spectral and X-ray structural characterization Full article

Journal

Organometallics
ISSN: 0276-7333

Output data

Year: 2007, Volume: 26, Number: 7, Pages: 1607-1615 Pages count : 9 DOI: 10.1021/om060883o

Authors

Voinov Maxim A. ² , Shevelev Tikhon G. ³ , Rybalova Tatyana V. ¹ , Gatilov Yury V. ¹ , Pervukhina Natalie V. ³ , Burdukov Aleksei B. ³ , Grigor'ev Igor A. ¹

Affiliations

1	Institute of Organic Chemistry, Avenue Akad. Lavrent'eva 9, 630090, Novosibirsk, Russia
2	Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204
3	Institute of Inorganic Chemistry, Avenue Akad. Lavrent'eva 5, 630090, Novosibirsk, Russia

alpha-Organoelement-substituted nitrones have been synthesized for the first time through the reaction of the alpha-lithiated cyclic aldonitrones of 3-imidazoline 3-oxide, pyrroline 1-oxide, 2H-imidazole 1-oxide, and 3,4-dihydroisoquinoline 2-oxide series with electrophilic reagents such as HgCl2, (CH3)(3)SiCl, (C2H5)(3)GeCl, (n-C4H9)(3)SnBr, Ph2P(O)Cl, Ph2PCl, PhSSPh, PhSeSePh, TsCl, and TsF. Aldonitrones of the 3-imidazoline 3-oxide and pyrroline 1-oxide series were shown to readily afford the products of the lithiation-electrophilic substitution reaction. In contrast, aldonitrones of the 2H-imidazole 1-oxide and 3,4-dihydroisoquinoline 2-oxide series react smoothly only with halogen-free electrophiles. It was found that an aldonitrone group could be lithiated and selectively reacted with electrophiles even when kinetically more acidic methylene and amino groups are present in the molecule. Characteristic features of IR and C-13 NMR spectra of the compounds synthesized are discussed. Selected alpha-organoelement nitrones are characterized by an X-ray diffraction study.

Voinov M.A. , Shevelev T.G. , Rybalova T.V. , Gatilov Y.V. , Pervukhina N.V. , Burdukov A.B. , Grigor'ev I.A.
alpha-organoelement nitrones: Synthesis, properties, and IR and C-13 NMR spectral and X-ray structural characterization
Organometallics. 2007. V.26. N7. P.1607-1615. DOI: 10.1021/om060883o WOS Scopus РИНЦ

Published online:	Feb 22, 2007
Published print:	Mar 1, 2007

Web of science	WOS:000244958600013
Scopus	2-s2.0-34047253972
Elibrary	13546734
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