16812-43-4Relevant articles and documents
The first synthesis of 1,1,2-tristannylalkenes
Mitchell, T.N.,Kowall, B.
, p. 127 - 130 (2007/10/02)
The addition of tin-tin bonds to stannyl alkynes to generate 1,1,2-tristannylalkenes occurs readily in the presence of the catalyst system palladium bis(dibenzylideneacetone)/triethyl phosphite.
Selective Metalation of Bicycloocta-2,6-diene, II. Distannylated Derivatives and Stannylated Tricyclic Secondary Products
Hertkorn, N.,Koehler, F. H.
, p. 1405 - 1415 (2007/10/02)
Distannylated bicycloocta-2,6-diene (1) with (CH3)3Sn groups in positions exo-4 and 7 (7a), endo-4 and 7 (7b), exo-4 and 6 (7c), and probably exo-4 and endo-4 (7d) are obtained when 1 is treated first with an excess of n-BuLi/t-BuOK in alkane and then with (CH3)3SnCl.Byproducts are monostannylated derivatives of 1 and 1,4-bis(trimethylstannyl)but-2-ene (3).The formation of 7a/b/c is best understood when the two possible bicycloocta-2,6-dienyl dianions are generated as intermediates. 3, exo-4-Bis(trimethylstannylbicycloocta-2,6-diene (7e) is obtained from the corresponding dibromo derivative of 1 and (CH3)3SnLi with 3-bromo-exo-4-trimethylstannylbicycloocta-2,6-diene (9) as an intermediate.The bicyclic stannyl compounds are susceptible to a 1,5-homopentadienyl shift of a (CH3)3Sn group at relatively low temperature when the starting compound has the stannyl group in position 4 of 1 and when positions 6 or 7 are unsubstituted.Tricyclo2,7>oct-3-enes with (CH3)3Sn groups in positions exo-6 (5a), endo-6 (5b), 3 and exo-6 (10a), and 3 and endo-6 (10b) are thus obtained.On further heating, 10b gives 1-trimethylstannyl-3-vinylbenzene (11).All compounds have been studied systematically by NMR spectroscopy including δ(119Sn), δ(13C), δ(1H), 4/5J(119/117Sn-119Sn), nJ(119/117Sn-13C), nJ(119/117Sn-1H), 1J(13C-1H), and nJ(1H-1H).Among all nuclei, 119Sn gives the most simple spectra.From the 13C NMR spectra a series of useful increments of (CH3)3Sn groups emerges.The most interesting coupling constants are 5J(119/117Sn-119Sn), for which a considerable change with the dihedral angle is established, and nJ(119/117Sn-13C). For n = 3 and 4 the latter are especially useful because their angular dependence leads to unambiguous signal assignments. - Keywords: Bicycloocta-2,6-diene, Double Deprotonation, Stannyl Derivatives, Tricyclo2,7>oct-3-ene Derivatives, 119Sn, 13C, 1H NMR Spectra
SOME REACTIONS OF TRIS(TRIMETHYLSTANNYL)-AND TETRAKIS(TRIMETHYLSTANNYL)-METHANE
Hawker, Darryl W.,Wells, Peter R.
, p. 37 - 44 (2007/10/02)
With a variety of electrophilic reagents reaction occurs exclusively at the CH3-Sn bonds of 4C and 3CH.While the inner Sn-C bonds remain intact, methyl groups may be progressively cleaved off, one from each of the trimethylstannyl groups; in the case of bromine a second Me group may be cleaved from each of the SnMe2Br groups.The various products were identified by 1H, 13C and 119Sn MNR spectroscopy.
