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This study investigates the effectiveness of sludge in coagulation-flocculation treatment for suspended solids (SS) removal from landfill leachate using Tin (IV) chloride and Jatropha curcas seed (...

A tin(IV) chloride promoted (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles is reported. The transformation involves the Lewis acid assisted formation of 1,5-dipolar intermediates from the cyclopropane dicarboxylates and nitriles followed by cyclization. The reactions proceed in a highly diastereoselective manner and afford 5-vinyl-1-pyrroline derivatives in 60–88% yields.

A series of novel 1-(4-amino-6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-5-yl)-ethanones and 6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-4-amines were prepared by the annulation of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles with acetylacetone in the presence of tin(IV) chloride. The results demonstrated that the ethanones are the precursors of second compounds.

A series of novel N-acylsulfonamides derivatives were synthesized via direct condensation of parent sulfonamide with ethyl lactate as an acylating agent in the presence of tin (IV) chloride (SnCl4) as a Lewis acid catalyst. The sulfonamides were prepared, starting from chlorosulfonyl isocyanate (CSI), in three steps (carbamoylation, sulfamoylation, and deprotection) with excellent yields.

Leachate production from landfilling contributes crucial pollutants to the environment. This study examined the potential of tin (IV) chloride as coagulant that involved charge neutralization and sweep flocculation mechanisms. The negative charge of leachate is neutralized by adding tin (IV) chloride as cationic coagulant which resulted precipitation and swept most of the colloids and dissolved solids that entrapped in the settling as hydrous oxide floc. Parameters such as suspended solid (SS) content, color, and chemical oxygen demand (COD) were analyzed using standard jar test procedures. The best condition was observed at pH 8, with removal efficiencies of 75.99 %, 99.29 % and 98.36 % for COD, SS, and color, respectively. At optimum dosage, tin (IV) chloride successfully removed 98.40 % for color, 99.54 % for SS and 71.53 % for COD. These results indicated the satisfactory performance of tin (IV) chloride. Hence, tin (IV) chloride is a potential coagulant for the treatment of Alor Pongsu Landfill leachate.

The title compounds are partially condensed products of hydrolysed tri­methyl­tin chloride. In the two structures, short cationic tris­tannatoxanes (C9H29O2Sn3) are bridged by a diformatotri­methyl­tin anion or a chloride anion., The title compounds, [Sn3(CH3)9(OH)2(H2O)2][Sn(CH3)3(CHO2)2] (1) and [Sn3(CH3)9(OH)2]Cl·H2O (2), are partially condensed products of hydrolysed tri­methyl­tin chloride. In the structures of 1 and 2, short cationic tris­tannatoxanes (C9H29O2Sn3) are bridged by a diformatotri­methyl­tin anion or a chloride anion, respectively. Hydrogen bridges are present and supposedly stabilize these structures against further polymerization to the known polymeric tri­methyl­tin hydroxide. Especially noteworthy is that the formate present in this structure was formed from atmospheric CO2.

Thermal behavior of poly (methyl methacrylate) was analyzed in the presence of tin (IV) chloride. Five different proportionspolymer to additivewere selected for casting films from common solvent. TG, DTG and DTA were employed to monitor thermal degradation of the systems. IR and py-GC-MS helped identify the decomposition products. The blends start degrading at a temperature lower than that of the neat polymer and higher than that of the pure additive. Complex formation between tin of additive and carbonyl oxygen (pendent groups of MMA units) was noticed in the films soon after the mixing of the components in the blends. The samples were also heated at three different temperatures to determine the composition of residues left after the expulsion of volatiles. The polymer, blends and additive exhibited a one step, two-step and three-step degradation, respectively. T0 is highest for the polymer, lowest for the additive and is either 60 o C or 70 o C for the blends. The amount of residue increases down the series (moving from blend-1 (minimum additive concentration) to blend-5 (maximum additive concentration)). For blend-1, it is 7% of the original mass whereas it is 16% for blend-5. Tmax also goes up as the concentration of additive in the blends is elevated. The complexation appears to be the cause of observed stabilization. Some new products of degradation were noted apart from those reported earlier. These included methanol, isobutyric acid, acid chloride, etc. Molecular-level mixing of the constituents and "positioning effect" of the additive may have brought about the formation of new compounds. Routes are proposed for the appearance of these substances. Horizontal burning tests were also conducted on polymer and blends and the results are discussed. Activation energies and reaction orders were calculated. Activation energy is highest for the polymer, i.e., 138.9 Kcal/mol while the range for blends is from 51 to 39 Kcal/mol. Stability zones are highlighted for the blends. The interaction between the blended parts seems to be chemical in nature.

A facile synthesis of potential acetylcholinesterase (AChE) inhibitors, the tacrine analogues 3a-p, has been accomplished by direct cyclocondensation of 1-aryl-4-cyano-5-aminopyrazole with β-ketoesters using tin(IV) chloride as catalyst. The structures of all the compounds have been confirmed by IR, ¹H- and ¹³C-NMR.

Formal [4 + 2] cycloaddition between various 3-ethoxycyclobutanones and allyltrialkylsilanes proceeded to give 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones by catalysis with tin(VI) chloride. The use of allyl-tert-butyldiphenylsilane induced 1,5-hydride transfer, which gave 2-[3-(tert-butyldiphenylsilyl)propyl]-6-methyltetrahydro-4-pyrones.

The rate of thermal decomposition of azobisisobutyronitrile (AIBN) dissolved in xylene was investigated alone and in the presence of tin(IV) chloride over the temperature range of 90-107 o C. It was found that the decomposition rate of AIBN increases linearly with increasing concentration of tin(IV) chloride, which suggests the formation of an activated complex between AIBN and tin(IV) chloride. A parallel reaction mechanism is proposed to describe the kinetic behavior. The Arrhenius relationships of rate constants were also obtained

The three isostructural compounds butyl­ammonium hexa­chlorido­tin(IV), pentyl­ammonium hexa­chlorido­tin(IV) and hexyl­ammonium hexa­chlorido­tin(IV), (CnH2n+1NH3)2[SnCl6], with n = 4, 5 and 6, respectively, crystallize as inorganic–organic hybrids. As such, the structures consist of layers of [SnCl6]2− octa­hedra, separated by hydro­carbon layers of inter­digitated butyl­ammonium, pentyl­ammonium or hexyl­ammonium cations. Corrugated layers of cations alternate with tin(IV) chloride layers. The asymmetric unit in each compound consists of an anionic component comprising one Sn and two Cl atoms on a mirror plane, and two Cl atoms in general positions; the two cations lie on another mirror plane. Application of the mirror symmetry generates octa­hedral coordination around the Sn atom. All compounds exhibit bifurcated and simple hydrogen-bonding inter­actions between the ammonium groups and the Cl atoms, with little variation in the hydrogen-bonding geometries.

Different tributyltin phenoxides react at room temperature with ethyl propiolate in benzene, in the presence of tin(IV) chloride, triethylamine and their mixture to give the derivatives of 3-phenoxyacrylic acid ethyl ester. Exceptionally, 3-(2-hydroxyphenyl)acrylic acid ethyl ester and 3-(2-hydroxy-5-methylphenyl)acrylic acid ethyl ester have been obtained from the reaction of tributylphenoxytin and tributyl(p-tolyloxy)tin, respectively catalysed by SnCl4, and they have been easily hydrolysed to coumarin and 6-methylcoumarin. Copyright © 2007 John Wiley & Sons, Ltd.

We have developed a new method of N-nitrosation of various secondary and tertiary amines, amides and ureas using a mixture oftin(IV) chloride and sodium nitrate. This method leads to a selective, high-yielding and mild heterogeneous N-nitrosation by in situ generation of nitrosyl chloride (NOCl). The reaction can be carried out in several different solvents such as chloroform, dichloromethane, ethers, ethyl acetate and alcohols, at room temperature.

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates when reacted with nitriles in the presence of tin(IV) chloride afford 2,4,5-trisubstituted oxazoles in good to excellent yields. The reactions take place through in situ generation of aroylmethylidene malonates from the cyclopropanes, followed by conjugate addition of nitriles to the malonates to form nitrilium ion intermediates and subsequent cyclisation.

Tin(IV) chloride selectively promotes the nucleophilic attack of methyl acetoacetate to the cyano instead of the olefinic carbon atom of α,β-unsaturated nitriles to give enaminoketoesters. In the presence of an excess of ketoester a second C–C bond formation occurs followed by cyclisation affording substituted pyridines in a selective cascade sequence.

The reaction of benzil with phenol at 180°C in the presence of SnCl4·5H2O produces a benzofuran, a benzofuranol, a benzodifuran, and a benzofuranone. Anhydrous tin(IV) chloride also gives a benzofuranofuranone. Other phenols and their methyl ethers yield related products. The good yields of the benzo- and naphtho-furanones make the method an attractive alternative to the benzilic acid route to such compounds.

2,3,5-Tri- O -benzoyl-β- d -ribofuranosyl cyanide reacts with methyl acetoacetate and diethyl malonate in the presence of stoichiometric amounts of SnCl 4 to give a β- d -ribofuranosyl-enaminoketoester and a β- d -ribofuranosyl-enaminodiester, respectively. The β- d -ribofuranosyl-enaminoketoester was debenzoylated, treated with 2,2-dimethoxypropane and tert -butyl-dimethylsilyl chloride to give the methyl 3-amino-3-(5′- O - tert -butyldimethylsilyl-2′,3′- O -isopropylidene-β- d -ribofuranosyl)-2-acetyl propanoate obtained in good yield together with small amounts of its α-anomer. The reactions of the β-anomer with hydrazine, methyl- and phenylhydrazine, carried out under controlled experimental conditions, afforded the pyrazole C-nucleosides in good yields as β-anomers.

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates when reacted with nitriles in the presence of tin(IV) chloride afford 2,4,5-trisubstituted oxazoles in good to excellent yields. The reactions take place through in situ generation of aroylmethylidene malonates from the cyclopropanes, followed by conjugate addition of nitriles to the malonates to form nitrilium ion intermediates and subsequent cyclisation.

The reaction of 1,4-dilithiotetraphenylbutadiene with germanium(IV) chloride and tin(IV) chloride affords heterocycles Ph4C4GeCl2, I and Ph4C4SnCl2, II. Compounds I and II, which feature a planar tetraphenylbutadiene backbone, were characterized by elemental analyses, 1H and 13C NMR spectroscopy and single crystal X-ray diffraction. The coordination environments for germanium and tin are distorted tetrahedra with bond angles spanning 35.35° for I and 24.86° for II. The Ge[sbnd]Cl and bond distances are 2.134 A and 2.143 A in I, while the Sn[sbnd]Cl and bond distances are 2.313 A and 2.312 A in II.

Using tin(IV) chloride, O -glycosylation reactions were performed on peracylated D-arabinofuranose, d -galactofuranose and l -rhamnofuranose as well as 1-bromo- d -arabinofuranoses at room temperature in good anomeric purities and yields. In these circumstances, this coupling method has certain advantages over standard glycosylation reactions, such as the Koenigs-Knorr methods which use the 1-halosugar (synthesized from the 1-acyl derivative) and toxic mercury salts as the coupling agent.

Direct treatment (1:1) of MCl3 (M = Sc, Y or La) with SnCl4 in thf provides colourless compounds of the type ScSnCl7(thf)5 and MSnCl7(thf)6 (M = Y, La), which have been characterised by elemental analysis and spectroscopic studies. An X-ray determination of ScSnCl7(thf)5 reveals an ionic structure comprising individual six-coordinate [ScCl2(thf)4]+ cations and [SnCl5(thf)]-anions. The cations feature an octahedral metal geometry in which a linear Cl-Sc-Cl unit is surrounded by an equatorial girdle of four solvent (thf) molecules.

The addition of diorganyl disulfides and dimethyl diselenide to cyclohexene in the presence of tin(IV) chloride proceeded stereoselectively affording trans-adducts of 1:1 composition. No reaction occurs in the absence of tin(IV) chloride.

Following observations on remote asymmetric induction using allylstannanes, 5-benzyloxy-4-methylpent-2-enylsilanes are also found to react with aldehydes with modest levels of 1,5-induction after treatment with tin(IV) chloride. Transmetallation to give intermediate allyltin trihalides may be involved.

The reaction of 5-fluorouracil with the seven-membered acetals 1a-g in the presence of tin (IV) chloride, trimethylchlorosilane and hexamethyldisilazane at room temperature gives 1-{[3-(2-hydroxyethylhetero)-1-alkoxy]alkyl}-5-fluorouracils 2a-f and 1-{[2-(3-hydroxypropoxy)-1-isopropoxy]ethyl}-5-fluorouracil 2g in 31–86% yields. The presence of an heteroatom on the 1-position of the cycloacetal and the use of tin (IV) chloride, capable of a 1,4-chelation, seem to impose their influence in the regiospecific ring opening of 1a-g. The conformational analyses carried out on 2b and (1R,3R)-2e and (1R,3S)-2e clearly indicate that the N1(sp2)-C1-C2-C3 moiety tends to fold in a gauche conformation. The antitumour activities of compounds 2b-g were assessed against HEp human cells showing that 2c is 4-fold more active than 5-FU. The drugs studied do not show any clear toxicity in comparison with the toxic effect of 5-FU.

Ortho-aminobenzonitriles 1 react with β-ketoesters and alkyl malonates, in the presence of stoichiometric amounts of tin(IV) chloride, to give 4-aminoquinolines 2 and 4-amino-2-quinolones 3 respectively. Similarly β-enaminonitriles 7 afford 4-aminopyridines 8 and 4-amino-2-pyridones 9.

The reaction of cyclic enaminonitriles1 with diethyl acetonedicarboxylate (2) affords fused 4-amino-3-ethoxycarbonyl-2-ethoxycarbonylmethyl-pyridines4. The course of the reaction and the yield of cyclic products were promoted by tin(IV)chloride. N-substituted diethyl 3-aminoglutaconates3 seem to be intermediates of the cyclization reaction.

2-Propenyl tin species, prepared from 3-halopropenes or 2-propenyl mesylate with tin(IV) chloride and tetrabutylammonium iodide in dichloromethane, causes nucleophilic addition to aldehydes to produce the corresponding homoallylic alcohols.

Transmetallation of the 5-benzyloxy-4-methylpent-2-en-1-yl(tributyl)- and -(triphenyl)stannanes 1 and 8 using tin(iv) chloride generates an allyltin trichloride that reacts with aldehydes to give (Z)-1,5-anti-6-benzyloxy-5-methylhex-3-en-1-ols 2. The allyltin trichloride believed to be the key intermediate in these reactions has been trapped by phenyllithium to give anti-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 9. Transmetallation of this anti-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 9 generated an allyltin trichloride that reacted with aldehydes to give the (Z)-1,5-syn-6-benzyloxy-5-methylhex-3-en-1-ols 23 and was trapped by phenyllithium to give syn-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 24. Similar stereoselectivity was observed for tin(iv) chloride promoted reactions of this syn-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 24 with aldehydes and with phenyllithium. The allyltin trichlorides generated by transmetallation of 4-hydroxy- and 4-benzyloxy-pent-2-enyl(triphenyl)stannanes 34 and 35 were similarly trapped by phenyllithium to give 4-hydroxy- and 4-benzyloxy-pent-1-en-3-ylstannanes 36 and 37 whose configurations were established by correlation with known compounds. This work confirmed the configurations of the intermediate allyltin trichlorides involved in tin(iv) chloride promoted reactions of 4- and 5-alkoxypent-2-enylstannanes with aldehydes and showed that the high levels of remote stereocontrol were due mainly to kinetically controlled transmetallation. A fuller mechanistic scheme is proposed for the reactions in the 5-benzyloxy-4-methylpent-2-enylstannane series together with relevant (119)Sn NMR data.

Transmetallation of (S)-4-benzyloxy-2-pentenyl(tributyl)stannane (I) using tin(IV) chloride generates an allyltin trichloride which reacts in situ with aldehydes to give 1-substituted syn-(3Z)-5-benzyloxyhexenols with excellent stereoselectivity. With chiral aldehydes, the stereoselectivity of the reaction is dominated by the reagent, except for 2-alkoxyaldehydes which show matching and mismatching consistent with preferred Felkin-Anh diastereofacial selectivity

The synthesis of C7- to C16-alkyl maltosides in the presence of tin(IV) chloride as Lewis acid catalyst was performed. The characterization of the products and theoretical investigation of the crucial step in the synthesis were carried out. The preparation of the β-maltosides required reaction time of 1 h, and that of the α-maltosides was 72 h. The side products were the α-D-maltosidechloride and 2-hydroxy-β-maltoside, respectively. The PM3 calculation confirmed the formation of the kinetically controlled β-product. KEY WORDS : Maltose, Synthesis of maltosides, Tin(IV) chloride, PM3 Bull. Chem. Soc. Ethiop. 2011 , 25(1), 83-90.

Tin(IV) chloride catalyzed inverse electron demand hetero-Diels-Alder reaction of substituted methyl 2-oxo-3-alkenoates with simple alkenes led to methyl 3,4-dihydro-2H-pyran-6-carboxylates in satisfactory yields. The addition proceeded stereospecifically through an exo transition state.

In the presence of a catalytic amount of tin(IV) species generated from tin(IV) chloride and silver perchlorate, 1-O-acetyl-D-glucose stereoselectively reacts with silyl alkoxides to give the corresponding α-glucosides in high yields.

The cross-coupling reaction of allylstannanes with allylsilanes selectively proceeded in the presence of tin(IV) chloride to give 1,5-dienes. It was found that the substitution of a phenylthio group at γ-position remarkably increased the reactivity of allylstannanes.

Transmetallation of (S)-4-benzyloxy-2-pentenyl(tributyl)stannane (I) using tin(IV) chloride generates an allyltin trichloride which reacts in situ with aldehydes to give 1-substituted syn-(3Z)-5-benzyloxyhexenols with excellent stereoselectivity. With chiral aldehydes, the stereoselectivity of the reaction is dominated by the reagent, except for 2-alkoxyaldehydes which show matching and mismatching consistent with preferred Felkin-Anh diastereofacial selectivity

Ortho-aminobenzonitriles 1 react with β-ketoesters and alkyl malonates, in the presence of stoichiometric amounts of tin(IV) chloride, to give 4-aminoquinolines 2 and 4-amino-2-quinolones 3 respectively. Similarly β-enaminonitriles 7 afford 4-aminopyridines 8 and 4-amino-2-pyridones 9.

Following observations on remote asymmetric induction using allylstannanes, 5-benzyloxy-4-methylpent-2-enylsilanes are also found to react with aldehydes with modest levels of 1,5-induction after treatment with tin(IV) chloride. Transmetallation to give intermediate allyltin trihalides may be involved.

Using tin(IV) chloride, O -glycosylation reactions were performed on peracylated D-arabinofuranose, d -galactofuranose and l -rhamnofuranose as well as 1-bromo- d -arabinofuranoses at room temperature in good anomeric purities and yields. In these circumstances, this coupling method has certain advantages over standard glycosylation reactions, such as the Koenigs-Knorr methods which use the 1-halosugar (synthesized from the 1-acyl derivative) and toxic mercury salts as the coupling agent.

The reaction of benzil with phenol at 180°C in the presence of SnCl4·5H2O produces a benzofuran, a benzofuranol, a benzodifuran, and a benzofuranone. Anhydrous tin(IV) chloride also gives a benzofuranofuranone. Other phenols and their methyl ethers yield related products. The good yields of the benzo- and naphtho-furanones make the method an attractive alternative to the benzilic acid route to such compounds.

Formal [4 + 2] cycloaddition between various 3-ethoxycyclobutanones and allyltrialkylsilanes proceeded to give 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones by catalysis with tin(VI) chloride. The use of allyl-tert-butyldiphenylsilane induced 1,5-hydride transfer, which gave 2-[3-(tert-butyldiphenylsilyl)propyl]-6-methyltetrahydro-4-pyrones.

The cross-coupling reaction of allylstannanes with allylsilanes selectively proceeded in the presence of tin(IV) chloride to give 1,5-dienes. It was found that the substitution of a phenylthio group at γ-position remarkably increased the reactivity of allylstannanes.

Monomeric non-cyclic and dimeric cyclic bis(amino)stannylenes react with tin(IV) chloride to give the corresponding bis(amino)tin dichlorides ( 1, 2 ) in essentially quantitative yield. By monitoring the exchange reaction between tin(IV) chloride and tetrakis(diethylamino)tin using 119 Sn NMR at low temperature, two intermediates ( 4, 5 ) were identified as binuclear complexes in which the tin atoms are bridged by two amino groups and one chloro ligand. The equilibrated 1:1 reaction mixture finally contains mainly bis(diethylamino)tin dichloride ( 3 ). The reaction between N,N ′-di-tert-butyl-1,3-diaminopropane/triethylamine (1:2) and SnCl 4 affords the cyclic bis(amino)tin dichloride ( 6 ) via elimination of HCl. The compounds 1–6 were characterized in solution by 1 H, 13 C, 29 Si and 119 Sn NMR. The solid state 119 Sn CP/MAS NMR spectrum of compound 6 proves that its monomeric character is retained also in the crystalline state.

Bis(1,5-cyclooctadiene)diiridium(I) dichloride [12112-67-3] [Ir(μ-Cl)(C8H12)]2 (MW 671.70) InChI = 1S/2C8H12.2ClH.2Ir/c2*1-2-4-6-8-7-5-3-1;;;;/h2*1-2,7-8H,3-6H2;2*1H;;/q;;;;2*+1/p-2/b2*2-1-,8-7-;;;; InChIKey = ZFOUDQNHNLDNLD-MIXQCLKLSA-L Alternate Name: di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I). Physical Data: mp 190–205 °C (dec). Form Supplied in: orange–red crystals. Solubility: soluble in organic solvents (dichloromethane, chloroform, 1,2-dichloroethane, acetone, acetonitrile, and others). Handling, Storage, and Precautions: harmful and irritant; solutions should preferably be handled under inert atmosphere. Tin(IV) chloride [7646-78-8] SnCl4 (MW 260.50) InChI = 1S/4ClH.Sn/h4*1H;/q;;;;+4/p-4 InChIKey = HPGGPRDJHPYFRM-UHFFFAOYSA-J Alternate Name: stannic chloride. Physical Data: bp 114 °C (lit.), mp −33 °C (lit.) d 2.226 g mL−1 at 25 °C (lit.). Form Supplied in: colorless liquid; fumes in moist air. Solubility: soluble in organic solvents (alcohol, diethyl ether, dichloromethane, 1,2-dichloroethane, benzene, toluene, xylene, and others); reacts violently with water. Handling, Storage, and Precautions: toxic and hygroscopic; therefore, it should be stored and handled under moisture-free atmosphere. Di-μ-chlorodichlorobis(1,5-cyclooctadiene)bis(trichlorostannyl)diiridium [851764-45-9] [Ir(C8H12)(μ-Cl)Cl(SnCl3)]2 (MW 1191.61) InChI = 1S/2C8H12.10ClH.2Ir.2Sn/c2*1-2-4-6-8-7-5-3-1;;;;;;;;;;;;;;/h2*1-2,7-8H,3-6H2;10*1H;;;;/q;;;;;;;;;;;;2*+2;2*+3/p-10/b2*2-1-,8-7-;;;;;;;;;;;;;; InChIKey = UECFXPBEOJTBIV-HVBPBDNUSA-D Alternate Name: Di-μ-chlorobis(1,5-cyclooctadiene)bis(trichlorostannyl)diiridium(III) dichloride. Physical Data: red microcrystals; mp 241–244 °C (dec). Solubility: soluble in coordinating solvents such as dimethylsulfoxide and acetonitrile at ambient temperature and in alcohol at higher temperature. Recovery of the compound from solution is difficult. Analytical Data: 1H NMR (200 MHz, DMSO-d6) δ(ppm) = 1.71–1.79 (br, m, 8H, CH2), 2.21–2.26 (br, m, 8H, CH2), 4.16 (br, s, 8H, CH). 13C NMR (54.6 MHz, DMSO-d6) δ(ppm) = 30.7 (CH2), 54.8 (CH), 73.6 (CH). Preparative Method: the reagent is prepared from bis(1,5-cyclooctadiene)diiridium(I) dichloride [Ir(μ-Cl)(C8H12)]2 and tin(IV) chloride (SnCl4).1 Handling, Storage, and Precautions: air and moisture stable in the solid state when minimally exposed; it is recommended to handle solutions under inert atmosphere. General Reactivity: for brevity in presentation, the bimetallic reagent [Ir(μ-Cl)Cl(COD)(SnCl3)]2 is hereafter represented as IrIII–SnIV, while a dual-reagent combination of [Ir(μ-Cl)(COD)]2 and SnCl4 (1:4 molar ratio) is represented as IrI/SnIV. Both the reagents are useful for benzylation of arenes and formation of triarylmethanes and carbon–heteroatom bonds.

Tin(IV) chloride catalyzed inverse electron demand hetero-Diels-Alder reaction of substituted methyl 2-oxo-3-alkenoates with simple alkenes led to methyl 3,4-dihydro-2H-pyran-6-carboxylates in satisfactory yields. The addition proceeded stereospecifically through an exo transition state.

β-Ketoesters and β-diesters react with β-enaminonitriles in the presence of stoichiometric amounts of tin (IV) chloride to give 4-aminopyridines and pyridones while they react with aromatic orthoaminonitriles to give 4-aminoquinolines and quinolones.

Treatment of (S)-4-benzyloxypent-(2E)-2-enyl(tributyl)stannane (3) with tin (IV) chloride at −78 °C, followed by the addition of an aldehyde, gives 1,5-diol derivatives (6) with excellent 1,5-diastereoselectivity.

[7646-78-8] Cl4Sn (MW 260.51) InChI = 1/4ClH.Sn/h4*1H;/q;;;;+4/p-4/f4Cl.Sn/h4*1h;/q4*-1;m InChIKey = HPGGPRDJHPYFRM-LUCXXLOKCB (strong Lewis acid used to promote nucleophilic additions, pericyclic reactions, and cationic rearrangements; chlorination reagent) Alternate Name: stannic chloride. Physical Data: colorless liquid; mp −33 °C; bp 114.1 °C; d 2.226 g cm−3. Solubility: reacts violently with water; sol cold H2O; dec hot H2O; sol alcohol, Et2O, CCl4, benzene, toluene, acetone. Form Supplied in: colorless liquid; 1 M soln in CH2Cl2 or heptane; widely available. Purity: reflux with mercury or P2O5 for several hours, then distill under reduced nitrogen pressure into receiver with P2O5. Redistill. Typical impurities: hydrates. Handling, Storage, and Precautions: hygroscopic; should be stored in a glove box or over P2O5 to minimize exposure to moisture. Containers should be flushed with N2 or Ar and tightly sealed. Perform all manipulations under N2 or Ar. Solvating with H2O liberates much heat. Use in a fume hood.

Tin(IV) chloride selectively promotes the nucleophilic attack of methyl acetoacetate to the cyano instead of the olefinic carbon atom of α,β-unsaturated nitriles to give enaminoketoesters. In the presence of an excess of ketoester a second C–C bond formation occurs followed by cyclisation affording substituted pyridines in a selective cascade sequence.

Pyrazolo[3,4- b]pyridines have been obtained by the condensation of 5-amino-4-cyanopyrazole, readily available by the reaction of dithioacetals with substituted hydrazines, with β-ketoesters or β-diketone in the presence of tin(IV) chloride at reflux temperature in dry toluene.

Activated acetophenones were deacetylated by treatment with an excess of tin(IV) chloride in 1,2-dichloroethane.