Tri-w-butyltin Hydride

As for organogermanium hydrides, a simple organotin hydride, like tri-w-butyltin hydride, can be used for the reduction of structurally more complicated diorganotin dichlorides228 ... 

A convenient preparation of tri-w-butyltin hydride is the hydrogenation of (Bu3Sn)20 with NaBH4 in EtOH, giving the hydride in 95% yield after 30 minutes reaction229. 

Treatment of L-Ser-OMe with 3-bromocyclopentene after the hydroxy group was replaced with iodide gave in the presence of 2,2 -azobisisobutyro-nitrile (AIBN) and tri-w-butyltin hydride a mixture of stereoisomers. These stereoisomers were separated and transformed into (lS,35,5S)-54 and (lR,35,5R)-isomer 55, which are precursors of the potent angiotensinconverting enzyme inhibitors [89H(28)957], Isomer 54 was also obtained from N-acetylserine methyl ester which was converted into its chloro analog and reacted with cyclopentenepyrrolidine (84TL4479). 

Other reactive forms of nickel including nickel boride and nickel alkoxide complexes can also be used for desulfurization. Tri-w-butyltin hydride is an alternative reagent for desulfurization.204... 

Alcohols Iodotrimethylsilane. Sodium borohydride. Tri-w-butyltin hydride. 

Moreover, an a-deutero substituent does not have any effect on the stereochemical outcome. Both mixtures (70 30 and 3 97) of cis- (67) and rmns-1-bromo-l-deutero-2-phenylcyclopropane (68) gave, upon reduction with tri-w-butyltin hydride, the same mixture (95 5) of cis- (69) and rrans-l-deutero-2-phenylcyclopropane (70). ... 

A radical cyclization has been used by Hart, at The Ohio State University, to prepare the manzamine tricyclic core (139). Utilizing tri-w-butyltin hydride to mediate the cyclization of selenide 171, the desired stereochemistry of the octahydroisoquinoline ring (172) was established (Scheme 13) electrophilic catalysis generated the tricyclic intermediate 174. An anionic cyclization leading to a tricyclic intermediate is being developed by Marko, at the University of Sheffield, toward which he has recently reported a model study (140). 

Reductive Dehalogenation with Tri-w-butyltin Hydride A Powerful New Technique for Use in Poly(vinyl chloride) Microstructure Investigations... 

Tri-n-butylstannyllithiiim, (n-C4H9)3SnLi (1). Mol. wt. 296.97. The reagent is prepared most conveniently by deprotonation of tri-w-butyltin hydride with LDA in THF at 0° (about quantitative yield). f... 

Reduction of the vinyl halide, j8-bromostyrene, at 100° C with tri-w-butyltin hydride provided only 35% of styrene, presumably because of hydrostannation of some of the styrene under the reaction conditions. Aryl halides can be reduced satisfactorily under fairly drastic conditions (66, 77). For example, 1- and 2-bromonaphthalenes have been reduced by triphenyl-tin hydride in 31% and 69% yields, respectively, at 150° C in 15 hours. Several -substituted halobenzenes have been studied, as shown in Table XII. There is an indication that electron-releasing substituents hinder reaction and electron-withdrawing substituents have the opposite effect. However the facilitation by the phenyl group complicates the picture. 

Tri-/ -butyltin hydride also serves as a hydrogen-atom donor in radical-mediated methods for reductive deoxygenation of alcohols.131 The alcohol is converted to a thiocarbonyl derivative. These thioesters undergo a radical reaction with tri-w-butyltin... 

W. P. Neumann, Synthesis, 1987, 665 discusses the reduction of acyl halides to aldehydes with tri-n-butyltin hydride. 

Neumann, W.P. (1987) Tri- i-butyltin Hydride as Reagent in Organic Synthesis, Synthesis, 665-683. 

Di-w-butyltin dihydride reduces halides somewhat more easily than tri-n-butyltin hydride. Yields of reduction products isolated from typical halides are 2-bromooctane, 99% 1-bromooctane, 84% bromocyclo-hexane, 82% benzyl bromide, 60% benzyl chloride, 83% 3-bromo-camphor, 79%. 

J.J. Sullivan, J.D. Torkelson, M.W Wekell, A. Hollingsworth, WL. Saxton, G.A. Miller, K.W Panaro, and A.D. Uhler. Determination of tri-n-bulyltin and di-ra-butyltin in fish as hydride derivatives by reaction gas chromatography. Anal. Chem., 60, 626 (1988). 

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