Abstract
Arbuzov reactions of the fluorous primary iodides Rfn (CH2 )m I [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 )m P(O)(OEt)2 (56-59%), which are reduced with LiAlH4 to the title compounds Rfn (CH2 )m PH2 (62-78%). Fluorophilicities (CF3 C6 F11 /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 )m NH2 > Rfn (CH2 )m PH2 > Rfn (CH2 )m P(O)(OEt)2 .
Key words
phosphines - phosphonates - Arbuzov reaction - fluorous - partition coefficients
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