Synthesis

Convenient and Convergent Syntheses of Long-Chain α, ω-Dibromides and Diphosphines of the Formula X (CH2) nX (n= 18-32)

W Mohr, CR Horn, J Stahl, JA Gladysz

Index: Mohr, Wolfgang; Horn, Clemens R.; Stahl, Juergen; Gladysz Synthesis, 2003 , # 8 p. 1279 - 1285

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Citation Number: 13

Abstract

Abstract The known tetrahydropyranyl ethers Br (CH 2) y OTHP (y= 6, 9, 11), which are easily prepared from commercial bromoalcohols, are sequentially treated with Mg, Li 2 CuCl 4, and X (CH 2) z X (z/X= 6/Br, 7/Br, 8/Br, 10/Br, 10/I) to give the diethers THPO (CH 2) n OTHP in 68-40% yields (n= 2 y+ z= 18, 19, 20, 22, 24, 28, 32). Subsequent reactions with Ph 3 P and 2, 4, 4, 6-tetrabromocyclohexa-2, 5-dienone give the title compounds Br (CH 2) n ...