One-step preparation, structural assignment, and X-ray study of 2,2-di-n-butyl- and 2,2-diphenyl-6-aza-1,3-dioxa-2-stannabenzocyclononen-4-ones derived from amino acids

Chemistry : a European Journal
Hiram I BeltránNorberto Farfán

Abstract

Twenty-four 2,2-di-n-butyl- and 2,2-diphenyl-6-aza-1,3-dioxa-2-stannabenzocyclononen-4-ones, each having a transannular N-->Sn bond, have been prepared by one-step reactions of alpha-amino acids (1 a-l), salicylaldehyde (2), and either di-n-butyltin(IV) oxide (3) or diphenyltin(IV) oxide (4). The new methodology constitutes an easy, highly efficient one-step synthesis of diorganotin(IV) derivatives, such as 5 a-l and 6 a-l, from iminic tridentate ligands without isolation of the Schiff bases. The structures of all the compounds have been established by a combination of (1)H, (13)C, (15)N, and (119)Sn NMR spectroscopy, IR spectroscopy, mass spectrometry, and elemental analysis. In all cases, the (119)Sn chemical shifts, as well as the (1)J((119)Sn,(13)C) coupling constants, are indicative of pentacoordinated tin atoms in solution. The structures of compounds 5 a, d, f, 6 a, b, b-racemic, c, d, f, g, and l have been established by single-crystal X-ray diffraction analyses. The tin atoms in 5 d, f, 6 a, b, b-racemic, c, d, g, and l each have a distorted trigonal-bipyramidal (TBP) geometry, with the oxygen atoms from the phenol and carboxylate moieties occupying the axial positions, and the imine nitrogen and phenyl or n-butyl subs...Continue Reading

Citations

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