Reactions of Bis-(Triethyltin) Oxide with Acids. Triethyltin Mercaptides

Sasin, George S.

doi:10.1021/jo50015a012

Cited by 35 publications

(7 citation statements)

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“…Some (alky1thio)triethyltin con~pounds have been prepared similarly from triethyltin oxide and an excess of alkanethiol: the excess thiol and water were removed from the product by distillation (4). These reactions show the relatively acidic nature of the S-H hydrogens in thiols, and is in agreement with the observation that an -OR group can be displaced by the -SR group of thiols in organotin compounds The tin-sulfur bond in organotin sulfur derivatives can be fractured by bromine, forming an organotin bromide and a disulfide: a similar reaction has been reported as occurring with iodine, but no details are given (1).…”

Section: Discussionmentioning

confidence: 99%

Preparation of some organotin compounds containing methylthio, phenylthio, and pentafluoro-phenylthio groups

Peach¹

1968

Can. J. Chem.

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The new compounds n-Bu3SnSR, n-Bu2Sn(SR)2, where R = Me, Ph, or C6F5, and Ph3SnSC6F5 have been prepared and characterized. The fracture of the Sn—S bond with iodine has been examined and affords a quantitative method for analysis of compounds containing a Sn—S bond. The 1H and 19F n.m.r. have been studied; frequencies characteristic of the C6F5S— group in the infrared spectra have been tabulated.

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Section: Discussionmentioning

confidence: 99%

Preparation of some organotin compounds containing methylthio, phenylthio, and pentafluoro-phenylthio groups

Peach¹

1968

Can. J. Chem.

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“…The reported boiling point at 1 mm. and the index of refraction for this compound are 132-135°and 1.5740 respectively (10). Anal.…”

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confidence: 86%

“…By repeated recrystallization from petroleum ether, the melting point was raised to 122-123°. The reported melting point is 107°and the reported boiling point is 218° ( 10). Anal.…”

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Reactions of Tetraethyltin With Organic Acids

Sasin¹,

Sasin²

1955

J. Org. Chem.

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This paper reports the cleavage of ethyl groups from tetraethyltin by organic acids whose ionization constants range between 10-1 and 10-10. SUMMARY 1. Cleavage reactions of tetraethyltin were studied. 2. The following previously unreported compounds were prepared: triethyltin monochloroacetate, dichloroacetate, ß-naphthyl mercaptide, phenyl mercaptide, n-heptyl mercaptide, and n-hexyl mercaptide.Philadelphia 4, Pennsylvania

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“…n-Butyltin trichloride was available through the courtesy of Metal & Thermit Corp., New York, N. Y. Preparation of large amounts of (Et3Sn)20 and (Et3Sn)2S followed the published directions (2) or modifications thereof. Recent publications describe the preparation of EtgSnSMe (3), Me2Si(OCOCF3)2 and MeSi(OCOCF3)3 (6), MeOSi(NCO)a (7), MegSiNCS (8), EtgSi(CN) (9),DodSiIa (10), n-PrsGeF (11), and iso-PraGeOH (12).…”

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Reactions With Esters, Halides, and Halogenoids. I. Bis-(Triethyltin) Oxide and Sulfide

Anderson¹

1954

J. Org. Chem.

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In Group IV-regular there is a gradual increase in basicity from the nearly neutral carbon to the clearly basic tin; this order of increasing basicity depends on experimental results mainly in aqueous or non-aqueous solutions.An exploratory publication on organogermanium esters established (Et3Ge)20 as the most basic, (Et2GeO)4 as the next most basic and [(EtGeO)20]n as the least basic ethylgermanium oxide (1). This work suggested that bis-(trialkyltin) oxides would react with numerous acids weaker than acetic acid; recent researches at this Institute demonstrate the reaction of (Et3Sn)20 with H2S or C2H6SH (2), or with HCN (3). This present paper, exploratory in nature, clearly demonstrates the capture of halogen, halogenoid, or an ester group by tin at the expense of silicon, germanium, phosphorus, arsenic, or antimony. It also shows the transfer of halogen from tin of a higher oxidation number to tin of a lower oxidation number.

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Reactions of Bis-(Triethyltin) Oxide with Acids. Triethyltin Mercaptides

Cited by 35 publications

References 2 publications

Preparation of some organotin compounds containing methylthio, phenylthio, and pentafluoro-phenylthio groups

Preparation of some organotin compounds containing methylthio, phenylthio, and pentafluoro-phenylthio groups

Reactions of Tetraethyltin With Organic Acids

Reactions With Esters, Halides, and Halogenoids. I. Bis-(Triethyltin) Oxide and Sulfide

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