Octadecane, 7 8-dichloro

This procedure is general for the conversion of epoxides to dichlorides with inversion of configuration at each of the two carbons and, in effect, provides a method for the cis-addition of chlorine to a double bond.2 ci.v-1,2-Dichlorocyclohcxane has also been prepared from 1,2-epoxycyclohexane and sulfuryl chloride,3 but the stereospecificity of the reaction appears to be extremely sensitive to reaction conditions, and the yield is lower than that obtained by the method described here. Other methods give cis-1,2-dichlorocyclohexane contaminated with considerable amounts of the trans -isomer. This method has been used to convert cis- and trans-4,5-epoxyoctanes to meso- and d/-4,5-dichlorooctanes, respectively, and trans-7,8-epoxyoctadecane to fhreo-7,8-dichloro-octadecane. These conversions were carried out on smaller amounts of material, and the products were purified by column chromatography on silica gel. Yields were 51-63%. 

ClsHi8CI2 f 4,4 -Dichloro-a, diethylstilbene, 32B, 43 Ci8H38f n-Octadecane, 27, 743 38B, 59 CisHagO, Tetra-t-butylacetone, 39B, 30... 

C2 Ha aBrNOa 9 2-p-Bromophenyl-4a,5,5a,6,7,8,9,9a,10,10a-decahydro-5a-methyl-10a-morpholino-4H-naphtho[2,3-b]pyran, 40B, 336 C211H3fiNeO, N,N -Bis-(2-cyanoethyl)-l, 10-diaza-4,7,13,16-tetraoxa-cyclo-octadecane malononitrile complex, 45B, 417 C25H20CINO13, 6,7-Bis(methoxycarbonyloxy)-l,2,3,4-tetrahydro-iso-quinoline-[1,2-c]-oxazol-2-one-[3,4-b]-1-chloro-3-methoxycarbonyl-oxy-6,7-methylenedioxyindane, 45B, 418 C2 5H21 Cl2NO, 3-(3,5-Dichloro-2,4,6-trimethylphenyl)-4-diphenylmeth-ylene-2-isoxazoline, 42B, 283... 

C12 2 Cl20i,PdS2, cis DichlorO (4,7,13,1 6-tetraoxa-1, 1 0-dithiacyclo-octadecane)palladium(II), 4OB, 1005 C12 2 ftCuNgOsSft, Tetrakis(imidazoline-2-thionato)copper(I) nitrate, 42B, 936... 

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