Efficient Syntheses of Fluorous Primary Phosphines that Do Not Require PH 3 Academic Article uri icon

abstract

  • Arbuzov reactions of the fluorous primary iodides Rfn(CH 2)mI [Rfn = CF3(CF2) n-1; n/m = 6/2, 8/2, 8/3, 10/2] and P(OEt)3 (excess, 160°C) give the fluorous phosphonates Rfn(CH2) mP(O)(OEt)2 (56-59%), which are reduced with LiAlH 4 to the title compounds Rfn(CH2) mPH2 (62-78%). Fluorophilicities (CF3C 6F11/toluene partition coefficients) increase with the length of the Rfn moiety, decrease with the length of the (CH 2)m moiety, and decrease in the functional group sequence Rfn(CH2)mNH2 > R fn(CH2)mPH2 > R fn(CH2)mP(O)(OEt)2. © Georg Thieme Verlag Stuttgart.

author list (cited authors)

  • Emnet, C., & Gladysz, J. A.

citation count

  • 2

publication date

  • January 2005