Abstract
Arbuzov reactions of the fluorous primary iodides Rfn(CH2)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 LiAlH4 to the title compounds Rfn(CH2)mPH2 (62-78%). Fluorophilicities (CF3C6F11/toluene partition coefficients) increase with the length of the Rfn moiety, decrease with the length of the (CH2)m moiety, and decrease in the functional group sequence Rfn(CH2)mNH2 > Rfn(CH2)mPH2 > Rfn(CH2)mP(O)(OEt)2.
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