Abstract

(E) [6386-72-7] C3H5Li (MW 48.02) InChI = 1S/C3H5.Li/c1-3-2;/h1,3H,2H3; InChIKey = MXFRWBNCSXHXRE-UHFFFAOYSA-N (Z) [6524-17-0] InChI = 1S/C3H5.Li/c1-3-2;/h1,3H,2H3; InChIKey = MXFRWBNCSXHXRE-UHFFFAOYSA-N (precursor of propenyl metals2) Physical Data: 1H and 13C NMR spectra have been reported.2g Preparative Method: prepared by reaction of 1-chloro- or 1-bromopropene with Lithium powder (containing 2% of sodium in the case of the chloride) in diethyl ether (eqs 1 and 2).4 This reaction occurs with a slight loss of stereochemistry.4d The reagent can also be prepared by metal–halogen exchange reaction between 1-bromopropene and t‐Butyllithium (eq 3),5 and by transmetalation of tin derivatives by an organolithium compound (eq 4).2g,6 In the two latter cases, the reactions are stereospecific. (1) (2) (3) (4) Handling, Storage, and Precautions: the solution of propenyllithium in diethyl ether must be handled with care since it is flammable and may ignite on contact with moisture and air. It should be stored and handled in an inert atmosphere (argon) and measured or transferred by means of a hypodermic syringe or cannula. The solution may deteriorate with time and the concentration of the reagent should be titrated before use.3

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