1178-79-6Relevant articles and documents
Synthesis of dineophyltin dihydride and stereoselective hydrostannation of alkynes and (E)-trisubstituted alkenes
Zú?iga, Adriana E.,Fidelibus, Pablo M.,Mandolesi, Sandra D.,Podestá, Julio C.
, p. 1547 - 1555 (2011/06/17)
This paper reports the synthesis of dineophyltin dihydride (3) following two procedures. The four steps synthesis starting from benzyl chloride and Sn was shown to be more convenient than the two step direct alkylation of SnCl 4. The study of the free radical hydrostannation of mono- and disubstituted acetylenes with hydride 3 shows that they are stereoselective and that the stereoisomers obtained in higher proportion are stable and easily separated by column chromatography. Some preliminary studies on the chemical reactivity of the new divinylsubstituted dineophyltin compounds in Stille reactions are also informed. Radical hydrostannatation of (E)-trisubstituted ethylenes with 3 did not succeed probably due to steric factors. The preparation of dineophyltin bromohydride (27) is also reported. Radical addition of 27 to methyl (E)-2,3-disubstituted propenoates leads to mixtures of the corresponding erythro and threo adducts in diastereomeric excesses (d.e.) in the range of 74-90%.
STERIC EFFECTS IN NEOPHILTIN(IV) CHEMISTRY
Lockhart, Thomas P.
, p. 179 - 186 (2007/10/02)
The stability and self-association in solution of (neophyl3Sn)2O, neophyl3SnOH, and (neophyl3Sn)2CO3 (neophyl = C6H5(CH3)2CCH2) have been examined by 119Sn NMR.The presence of Sn,Sn spin coupling through oxygen (2J(119Sn,117Sn)) has been used to distinguish between the distannoxane and stannol.Facile dehydration prevents the isolation of neophyl3SnOH from solution at room temperature and the equilibrium constant for H2O + (neophyl3Sn)2O 2neophyl3SnOH is 0.3 at 304 K.These observations are in sharp contrast with a previous report that the sterically bulky neophyl ligands render neophyl3SnOH stable toward dehydration. 1J(119Sn,13C) observed for neophyl3SnOH and (neophyl3Sn)2CO3 indicates that these compounds, unlike their n-alkyl-substituted homologues, are unassociated in solution, a result attributed to the steric bulk of the neophyl ligand.