2-Chloromethyl-3-tributylstannyl-1-propene

Abstract

[499157-71-0] C16H33ClSn (MW 379.58) InChI = 1S/C4H6Cl.3C4H9.Sn/c1-4(2)3-5;3*1-3-4-2;/h1-3H2;3*1,3-4H2,2H3; InChIKey = KRLTYKZSEPSTSX-UHFFFAOYSA-N (a bifunctional isobutene synthon that can act both as a nucleophile or electrophile in reactions common to allystannane and allyl chloride functional groups) Physical Data: bp 95–100°C (1.0 mmHg). Analysis of Reagent Purity: freshly prepared reagent has been characterized and judged pure by 1H NMR, 13C NMR, and elemental analysis. Solubility: soluble in organic solvents. Form Supplied in: colorless oil. Not commercially available. Preparative Methods: from 2-methyl-1-propene-3-ol through a two-step process involving reaction with n-BuLi and n-Bu3SnCl to form 2-[(tri-n-butylstannyl)methyl]-1-propen-3-ol followed by either Appel reaction or mesylation and displacement using LiCl (eq 1).1, 2 The reagent can also be prepared from commercially available 3-chloro-2-(chloromethyl)prop-1-ene by selectively displacing one of the two chlorine atoms with lithium tributyltin (eq 2).3 (1) (2) Purification: by distillation at 100–120 °C (0.4 mmHg) or by chromatography on silica gel eluting with hexanes or a mixture of hexanes and ether. Allylstannanes can be sensitive to residual acid and it may be necessary to conduct chromatography using silica gel that has been pretreated with triethylamine to prevent decomposition on the column. Handling, Storage, and Precautions: stable compound that can be handled safely provided good laboratory practice is observed. To prevent slow oxidation, store under inert atmosphere and refrigerate. Organotin compounds are toxic and can affect the central nervous system. Handling should take place only in a well-ventilated fume hood while using appropriate personal protective equipment to prevent exposure to the skin and eyes. Organotin compounds are considered harmful to the environment. Waste containing organotin compounds should be disposed of appropriately.