- Recycle of tin thiolate compounds relevant to ammonia-borane regeneration
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The use of benzenedithiol as a digestant for ammonia-borane spent fuel has been shown to result in tin thiolate compounds which we demonstrate can be recycled, yielding Bu3SnH and ortho-benzenedithiol for reintroduction to the ammonia-borane regeneration scheme.
- Sutton, Andrew D.,Davis, Benjamin L.,Bhattacharyya, Koyel X.,Ellis, Bobby D.,Gordon, John C.,Power, Philip P.
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p. 148 - 149
(2010/04/01)
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- Reductive carbon-sulfur bond cleavage: A simple pathway to nonstabilized (lithiomethyl)amines
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Compounds with the structural element -CH2NR2 are easily accessible from (phenylthiomethyl)amines by reductive C-S bond cleavage and subsequent addition or substitution. One advantage of this shorter method than tin- lithium exchange is the ready availability of the starting materials, which need not be purified by chromatography.
- Strohmann,Abele
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p. 2378 - 2380
(2008/10/09)
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- Generation of Aminyl Radicals using Sulfenamides as Synthetic Precursors
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Sulfenamides are synthesised from reaction between amines and N-(benzenesulfenil)-phthalimide or benzenesulfenyl chloride.The sulfenamides undergo reaction with tributyltin hydride to yield aminyl radicals which can be cyclised onto suitable alkenes. Key Words: sulfenamides; aminyl radicals; tributyltin hydride; radical-cyclisation; N-(benzenesulfenyl)phthalimide
- Bowman, W. Russell,Clark, David N.,Marmon, Robert J.
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p. 1275 - 1294
(2007/10/02)
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- REACTIVITY OF ALLYLIC AND VINYLIC SILANES, GERMANES, STANNANES AND PLUMBANES TOWARD SH2' OR SH2 SUBSTITUTION BY CARBON- OR HETEROATOM-CENTERED FREE RADICALS
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Compounds of the type CH2=CHCH2MR3 and (E)-PhCH=CHMR3 (M = Si, Ge, Sn, Pb) were allowed to react with a series of heteroatom-centered radicals (PhY*, Y = S, Se, Te, derived from PhYYPh) and carbon-centered radicals ((CH3)2CH* derived from (CH3)2CHHgCl).We report that alkenylplumbanes and, under forcing conditions, alkenylgermanes undergo SH2 or SH2' substitution of the metal by chain mechanism analogous to those previously reported for alkenylstannanes.Alkenylsilanes are unreactive.Based solely upon product yields, the following trends were observed: The reactivity of the alkenylmetals follow the order metal = Pb > Sn > Ge (> Si).The allylmetals were more reactive then the β-metallostyrenes toward the reactants employed in this study.The chalcogen series PhYYPh exhibits the reactivity order Y = S > Se > Te.
- Light, James P.,Ridenour, Michael,Beard, Lois,Hershberger, James W.
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- Organotin-Mediated Selective Desulfurization: Tri-n-butyltin Hydride Reduction of Unsymmetric Sulfides
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Tri-n-butyl hydride (TBTH) has been evaluated as a selective agent for the reductive cleavage of one C-S-bond in unsymmetric sulfides 1.Sulfides 1 (RR1) (where combinations of R and R1 included primary, secondary, tertiary, benzylic, phenyl, allylic, and α-(to carbonyl) carbon bound to sulfur> were each reacted with 1 equiv of TBTH in the presence of AIBN initiator.Reduction by TBTH occurs initially at the R1-S bond (where R1 can form the more stable carbon radical intermediate) in sulfide 1 selectively, if not specifically, to yield hydrocarbon 4 and tributylstannyl alkyl sulfide 3.However, this specifity can be negated by an enhanced reacitivity toward reduction by TBTH which the C-S bond in 3 exhibits, producing hydrocarbon 6 and bis(tributyltin) sulfide.The degree of selectivity in desulfurization is determined by the competition between unsymmetric sulfide 1 and alkyl organotin sulfide 3 for TBTH.The reduction of secondary and primary alkyl C-S bonds in 1 is so slow as to discount the synthetic utility of trialkyltin hydride reduction for such sulfides.
- Gutierrez, Carlos G.,Summerhays, Leo R.
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p. 5206 - 5213
(2007/10/02)
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