Abstract
Tetraorganotin tin(IV) compounds containing a flexible or rigid (4: Ph3Sn-CH2-C6H4-R; 7: Ph3SnC6H4-R, R = 2-oxazolinyl) chelating oxazoline functionality were prepared in good yields by the reaction of lithiated oxazolines and Ph3SnCl. Reaction of 7 with excess HCl resulted in the isolation of the tin monochlorido compound, 9 (ClSn[Ph2]C6H4-R). Conversion of the triphenylstannanes 7 and 4 into their corresponding dibromido species was successfully achieved from the reaction with Br2 to yield 10 (Br2Sn[Ph]C6H4-R) and 11 (Br2Sn[Ph]-CH2-C6H4-R), respectively. X-ray crystallography of 4, 7, 9, 10, and 11 reveal that all structures adopt a distorted trigonal bipyramidal geometry around Sn in the solid state. Compound 4, with an additional methylene spacer group, displays a comparatively long Sn–N bond distance compared to the dibromido tin species, 11. Several DFT methods were compared for accuracy in predicting the solid-state geometries of compounds 4, 7, 9–11. Compounds 10 and 11 were further converted into the corresponding dihydrides (12: H2Sn[Ph]C6H4-R, 13: H2Sn[Ph]-CH2-C6H4-R), via Br–H exchange, in high yield by reaction with NaBH4. Polymerization of 12 or 13 with a late transition metal catalyst produced a low molecular weight polystannane (14: –[Sn[Ph]C6H4-R]n–, Mw = 10,100 Da) and oligostannane (15: –[Sn[Ph]-CH2-C6H4-R]n–, Mw = 3200 Da), respectively.
Highlights
Polystannanes are main group polymers consisting of chains of covalently bonded tin atoms
These materials possess unique chemical, optical, and electronic properties attributed to the delocalization of the formal Sn 5s electrons into σ–σ bonding orbitals along the backbone [1]. The degree of such delocalization in polystannanes is greater than that noted for comparable Group 14 polymers
13C, 15N and 117Sn NMR spectroscopy. Synthesis of these were probed effectively by 1H,was hypercoordinated compounds achieved via bromine-lithium exchange from a 2-(2′0 -bromophenyl)-2-oxazoline ring (n-BuLi) followed by reaction bromine-lithium exchange from a
Summary
Polystannanes are main group polymers consisting of chains of covalently bonded tin atoms. Polystannanes attributed to the flexible side chain containing a donor atom that can move freely to, and away from, bearing more Polystannanes rigid groups dobearing not sharemore the same of flexibility, resulting stronger tin centers. We disclosed detailspolystannanes on the preparation of hypercoordinate polystannanes with (2-methoxymethyl) chelating group [17] These materials are derived by dehydropolymerization of the benzyl κ -C,N (dimethylamino) or a κ -C,O (2-methoxymethyl) chelating group [17]. Synthesis of these were probed effectively by 1H,was hypercoordinated compounds achieved via bromine-lithium exchange from a 2-(2′0 -bromophenyl)-2-oxazoline ring (n-BuLi) followed by reaction bromine-lithium exchange from a. 2-(2 hypercoordinated compounds was achieved bromine-lithium fromThis a 2-(2′bromophenyl)-2-oxazoline ring (n-BuLi) followedvia by reaction with a tin exchange halide species.
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