Convenient and Convergent Synthesesof Long-Chain α,ω-Dibromides and Diphosphinesof the Formula X(CH 2 ) n X (n = 18-32)
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The known tetrahydropyranyl ethers Br(CH2)yOTHP (y = 6, 9, 11), which are easily prepared from commercial bromoalcohols, are sequentially treated with Mg, Li2CuCl4, and X(CH2)2X (z/X = 6/Br, 7/Br, 8/Br, 10/Br, 10/I) to give the diethers THPO(CH2)nOTHP in 68-40% yields (n = 2 y + z = 18, 19, 20, 22, 24, 28, 32). Subsequent reactions with Ph3P and 2,4,4,6-tetrabromocyclohexa-2,5-dienone give the title compounds Br(CH2)nBr in 91-75% yields. Reactions with commercial K+PPh2 give the diphosphines Ph2P(CH2)nPPh2 in 95-74% yields.
author list (cited authors)
Mohr, W., Horn, C. R., Stahl, J., & Gladysz, J. A.