Tin(IV) Chloride

作者: Stephen Castellino , David E. Volk , Calvin J. Chany

DOI: 10.1002/047084289X.RT113.PUB2

关键词: Inorganic chemistryTolueneHeptaneReagentLewis acids and basesChlorideBenzeneChemistrySolubilityTin(IV) chloride

摘要: [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 alcohol, Et2O, CCl4, benzene, toluene, acetone. Form Supplied in: colorless 1 M soln in CH2Cl2 or heptane; widely available. Purity: reflux mercury P2O5 for several hours, then distill under reduced nitrogen pressure into receiver P2O5. Redistill. Typical impurities: hydrates. Handling, Storage, Precautions: hygroscopic; should be stored a glove box over minimize exposure moisture. Containers flushed N2 Ar tightly sealed. Perform all manipulations Ar. Solvating H2O liberates much heat. Use fume hood.

参考文章(146)
G. E. Keck, S. Castellino, M. B. Andrus, Mechanistic Variability in the Lewis Acid-Promoted Reactions of Aldehydes with Organostannanes Selectivities in Lewis Acid Promoted Reactions. pp. 73- 105 ,(1989) , 10.1007/978-94-009-2464-2_5
Tatsuya Takahashi, Tsutomu Yokozawa, Takeshi Endo, Cationic polymerization of methoxyallene with Lewis acids Macromolecular Chemistry and Physics. ,vol. 192, pp. 1207- 1212 ,(1991) , 10.1002/MACP.1991.021920519
Andrea Boaretto, Daniele Marton, Giuseppe Tagliavini, Paolo Ganis, Allylstannation: X. Stereochemical course of the addition reactions of (E/Z-Bu3SnCH2CHCHCH3 with aldehydes in the presence of Lewis acids (Bu2SnCl2, BF3·Et2O, and TiCl4) Journal of Organometallic Chemistry. ,vol. 321, pp. 199- 207 ,(1987) , 10.1016/0022-328X(87)85039-8
Steven G. Wood, Krishna G. Upadhya, N. Kent Dalley, Patricia A. McKernan, Peter G. Canonico, Roland K. Robins, Ganapathi R. Revankar, Synthesis and biological activity of 5-thiobredinin and certain related 5-substituted imidazole-4-carboxamide ribonucleosides. Journal of Medicinal Chemistry. ,vol. 28, pp. 1198- 1203 ,(1985) , 10.1021/JM00147A013
David G. Bartholomew, Phoebe Dea, Roland K. Robins, Ganapathi R. Revankar, Imidazo(1,2-c)pyrimidine nucleosides. Synthesis of N-bridgehead inosine monophosphate and guanosine monophosphate analogues related to 3-deazapurines. Journal of Organic Chemistry. ,vol. 40, pp. 3708- 3713 ,(1975) , 10.1021/JO00913A019
Yoshinori Yamamoto, Norihiko Maeda, Kazuhiro Maruyama, Regioreversed addition of but-2-enyltributylstannane to aldehydes in the presence of aluminium chloride–propan-2-ol Journal of The Chemical Society, Chemical Communications. pp. 742- 743 ,(1983) , 10.1039/C39830000742
Masahiko Yamaguchi, Akio Hayashi, Masahiro Hirama, Carbometalation of ketone enolates with 1-alkynes: an alkylidenation reaction of silyl enol ethers promoted by stannic chloride-tri-n-butylamine (SnCl4-Bu3N) reagent Journal of the American Chemical Society. ,vol. 115, pp. 3362- 3363 ,(1993) , 10.1021/JA00061A058
Jean Paul Quintard, Bernard Elissondo, Michel Pereyre, (.alpha.-Ethoxyalkenyl)tins: new reagents for the synthesis of carbonyl compounds Journal of Organic Chemistry. ,vol. 14, pp. 1559- 1560 ,(1983) , 10.1021/JO00157A043
Augusto C. Veronese, Rosella Callegari, Carlo F. Morelli, Tin (IV) Chloride-promoted Synthesis of 4-Aminopyridines and 4-Aminoquinolines Tetrahedron. ,vol. 51, pp. 12277- 12284 ,(1995) , 10.1016/0040-4020(95)00773-2