S-Allyltetrahydrothiophenium Bromide

Robert A. Stockman

Robert A. Stockman

University of East Anglia, School of Chemical Sciences and Pharmacy, Norwich, UK

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First published: 14 March 2008

Abstract

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[66713-38-0] C7H13SBr (MW 209.14)

InChI = 1S/C7H13S.BrH/c1-2-5-8-6-3-4-7-8;/h2H,1,3-7H2;1H/q+1;/p-1

InChIKey = PYERPBAXHMULMS-UHFFFAOYSA-M

(reagent used as allyl carbene equivalent for the formation of vinyl epoxides1 and vinyl aziridines2 from aldehydes and imines, respectively)

Physical Data: mp 71.2–72.3 °C.

Solubility: sol H2O, alcohol, most organic solvents, not diethyl ether, petrol.

Preparation: equimolar amounts of tetrahydrothiophene and allyl bromide in a solvent (typically methanol3 or diethyl ether4) are left to stand for 24–48 h before the solution is evaporated to dryness under high vacuum. Trituration with petroleum ether3 or diethyl ether yields analytically pure material.

Handling and Storage: hygroscopic. Store under argon.

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