Convenient and convergent syntheses of long-chain alpha,omega-dibromides and diphosphines of the formula X(CH2)(n)X (n=18-32) Academic Article

abstract

• 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.

authors

• Gladysz, John

published proceedings

• SYNTHESIS-STUTTGART

author list (cited authors)

• Mohr, W., Horn, C. R., Stahl, J., & Gladysz, J. A.

citation count

• 3

complete list of authors

• Mohr, W||Horn, CR||Stahl, J||Gladysz, JA

publication date

• July 2003

publisher

• Thieme  Publisher

published in

• Synthesis  Journal

keywords

• Bromination
• Cross-coupling
• Grignard Reagents
• Phosphines
• Thp Ethers

Digital Object Identifier (DOI)

• 10.1055/s-2003-39414

start page

• 1279

end page

• 1285

volume

• 2003

issue

• 8

URL

• http%3A%2F%2Fdx.doi.org%2F10.1055%2Fs-2003-39414