Convenient stereoselective syntheses of the three isomeric 2, 6-octadienes

DM Walba, MD Wand, MC Wilkes

Index: Walba, David M.; Wand, Michael D.; Wilkes, Martin C. Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2259 - 2261

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Citation Number: 2

Abstract

H,.(d) Na/liquid NH,.(e) i, NaNH,, liquid NH,; ii, addition of Na'; iii, addition of CHJ (c) P-2 Ni catalyst, ethylenediamine, of (E)-and (Z)-2-butene. The Z, Z isomer has been conveniently obtained in an isomerically pure state by catalytic hydrogenation of 2, 6-0ctadiyne. 2~ The E, E isomer has been obtained by the nickel carbonyl promoted coupling of 1-chloro-Zbutene and careful fractional distillation for removal of regioisomemZb To date, the E2 isomer has ...