Stannanes, trimethyl

Trimethylvinyltin Stannane, trimethyl vinyl- (8) Stannane, ethenyltrimethyl- (9) (754-06-3)... 

Besides halopyridazines, pseudohalopyridazines have been used as substrates for Stille reactions [29]. 6-Methylpyridazin-3-yl trifluoromethanesulfonate (96) reacted with arylstannanes using a procedure based on Stille s original conditions for aryl triflates. Although 3-methyl-6-(2-thienyl)pyridazine was obtained in a good yield (77%) under these conditions, trialkyl(phenyl)stannanes reacted only very slowly in comparison with tributyl(2-thienyl)stannane. Trimethyl(phenyl)stannane and tributyl (phenyl) stannane gave 3-methyl-6-phenylpyridazine in only 22 and 6% yield, respectively. 

Sm02C2sH44, Samarium(II), bis(Ti -penta-methylcyclopentadienyl)bis(tetra-hydrofuran)-, 27 155, 28 297 Sm03C42H63, Samarium, tris(2,6-di-tm-butylphenoxo)-, 27 166 Sm2Cl2Si4C44Hg4, Samarium, tetrakis T -l,3-bis(trimethylsilyl)cyclopentadienyl]di-p-chloro-di-, 27 171 SnCjHio, Stannane, trimethyl-, cobalt complex, 29 175, 178,180 SnCljPjC52H4, Stannate(l-), hexachloro-, 3,3,4,5-tetrahydro-l,l,33-tetraphenyl-lfM,2,3-triphospholium, 27 255 SnS4C24H2o, Tin(IV), tetrakis(benzenethio-lato)-,29 18... 

Two approaches for the synthesis of allyl(alkyl)- and allyl(aryl)tin halides are thermolysis of halo(alkyl)tin ethers derived from tertiary homoallylic alcohols, and transmetalation of other allylstannanes. For example, dibutyl(-2-propenyl)tin chloride has been prepared by healing dibutyl(di-2-propenyl)stannane with dibutyltin dichloride42, and by thermolysis of mixtures of 2,3-dimethyl-5-hexen-3-ol or 2-methyl-4-penten-2-ol and tetrabutyl-l,3-dichlorodistannox-ane39. Alternatively dibutyltin dichloride and (dibutyl)(dimethoxy)tin were mixed to provide (dibutyl)(methoxy)tin chloride which was heated with 2,2,3-trimethyl-5-hexen-3-ol40. 

Cyclohexenyl(trimethyl)stannane reacts with nonaromatic aldehydes with the usual selectivity, but with aromatic aldehydes with reduced, and in some cases reversed, stereoselectivity71. 

Trimethyl- und Triphenyl-chlor-stannan dimcrisieren in 1,2-Dimethoxy-athan/Tetrabutylammonium-perchlorat (Platinkathodc) zu Hexamethyl- bzw. Hexaphenyl-dizinn 3. 

In their search for new hgands with a very high binding affinity for the nicotinic acetylchohne receptor (nAChR), potentially useful in positron emission tomography (PET) when radiolabeled with [ F], Horti et al. described the synthesis of BOC-protected 5-(azetidin-2-ylmethoxy)-2-chloro-6 -fluoro-3,3 -bipyridine via a sequential classical heating and microwave irradiation of (2-fluoro-5-pyridinyl)(trimethyl)stannane with f-butyl 2- [(6-chloro-5-... 

The generation and recovery of stannane, methyl-, dimethyl-, and trimethyl-stannane were studied in seawater. Average tin recoveries for the six samples analysed, to which were added 0.4-1.6 ig methyltin compounds and 3ng inorganic tin, ranged from 96 to 109%. Reanalysis of analysed samples shows that all methyltin and inorganic tin is removed in one analysis procedure. 

Trimethvl Vinvlbenzvl Stannane—This procedure is identical to the preparation of trimethyl vinylbenzyl silane with the substitution of trimethyl tin chloride for the chlorotrimethyl silane. The following quantities were used 32.6 g (0.2136 mol) vinylbenzyl chloride in 65 mL of ether, 7.81 g (0.3211 mol) magnesium turnings. 

In analoger Weise, jedoch mit anderer Regioselektivitat, fuhrt die Reaktion von 2-Methyl-oxiran mit Diethylamino-trimethyl-stannan bzw. Piperidino-trimethyl-stannan zu den S-Trimethylstannyl-Derivaten der entsprechenden l-Dialkylamino-2-mercapto-propane, die mittels Malonsaure unter Bildung von l-Diethylamino-2-mercapto-propan (71%) bzw. 2-Mercapto-l-piperidino-propan (68%) gespalten werden konnen2 ... 

Alkynyl(trimethyl)silanes, germanes, and stannanes produce alkynyl-(phenyl)-A3-iodanes via ligand exchange on iodine under similar conditions [36]. Stang and co-workers developed a useful procedure for the preparation of diverse /3-functionalized alkynyl-A3-iodanes, which involves a ligand exchange of cyano-A3-iodane 19 with alkynylstannanes [37]. 

Synonyms TBTO bis(tributyltin) oxide oxybis (tributyltin) Stannane, bromomtriethyl- Chlorotrimethyl stannane chlorotrimethyltin trimethyl chlorotin Chlorotriphenyltin triphenylchloro- stannane... 

Aryltrimethyl stannanes are easily transformed into boronic acids by transmetalation with borane [106]. Thus, 1,4- and 1,3-Z>fy(trimethyl-stannanyl)benzenes as well as 2,5- and 2,6-Z /s(trimethylstannyl)pyridines synthesized by the SRN1 mechanism, react with borane in THF to give intermediates which on hydrolysis lead to benzene- and pyridinediboronic acids (Sch. 35) [107]. 

Thiophosphorsaure-O.S-diester-O-stannylester lassen sich aus Thi0phosphorsaure-O,O,S-triestern mit Jod-trimethyl-stannan herstellen (90-95%)624 ... 

Stereochemically pure allylsilanes and stannanes can also be obtained by metallation of suitable olefins with the superbasic mixture of butyllithium and potassium /fV/-butoxide followed by reaction with trimethylchlorosilane and tributylchlorostannane, respectively. In a representative example, 6-(2-tetrahydropyra-nyloxy)hex-l-ene is transformed into Z-(6-hydroxyhex-2-enyl)trimethylsilane through metallation with trimethyl-... 

The P —Te and As —Te bonds were not attacked by water5,6 or methanol5. Trimethyl-stannane similarly cleaved the group V element-tellurium bonds in these compounds5 and in their coordination compounds with chromium and molybdenum carbonyls7. 

Organotin reagents can be prepared 2-chloropyrimidine 901, for example, is stannylated by reaction with tributyl-, trimethyl-, or triphenylstannyllithium giving, e.g., 902. Stannanes can be obtained in the opposite sense too 4-iodo-2-methylthiopyrimidine can be stannylated by way of lithiation followed by quenching with a stannyl chloride. 

The same reactions have been found for M-methyl-substituted 2,2-diethyl-1,3,2-oxaazagermolidine (86) and 2,2-diethyl-1,3,2-diazagermolidine (772) dimethylamino(tri-n-butyl)germane and dimethylamino(trimethyl)stannane also undergo insertion into the E—N bond (2). 

While the large bulk of free-radical chemistry has been carried out using reagents such as tributyl, trimethyl and triphenyltin hydride, there are several examples of the use of designer stannanes that satisfy desired niche... 

The comparison of propene, allyltrimethylsilane, and isobutene indicates, that introduction of a trimethyl silyl group in /3-position of the developing carbenium center activates more than a methyl group in a-position. Both series of triphenyl element compounds (left and right column Scheme 44) show the reactivity pattern Si < Ge < Sn, but variation of the substituents at silicon and tin was found to largely affect the reactivity of the double bond. While in the allyl series (right column), the trialkylsilanes and -stannanes are 2 to 3 orders of magnitude more reactive than the... 

The reaction of trimethyl(perfluorophenyl)stannane with germanium(l V) chloride also proceeds smoothly, but the yield of trichloro(perfluorophenyl)germane (II. X = Cl) is rather low. Germanium(lV) bromide completely reacts with trimethyl(perfluorophcnyl)stannane over 22 hours. Apart from bromotrimethyltin. the reaction produces dibromodimethyltin. which makes it diflficult to isolate the target product. The reaction of germanium(IV) chloride with trimethyl(perlluorophenyl)silane does not proceed at a high temperature (240 C, 46 h), or in acetonitrile in the presence of cesium fluoride (50 C. 7 h). 

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