Convenient modular syntheses of fluorous secondary phosphines and selected derivatives Academic Article uri icon

abstract

  • Reactions of the fluorous primary phosphines Rfn(CH 2)2PH2 [Rfn = (CF2) n-1CF3; n = 6, 8, 10] and RfnCH=CH 2 [(n = 6, 8, 10) (1:1; THF, reflux) in the presence of AIBN give the title compounds [Rfn (CH2)2][R fn(CH2)2]PH [n/n = 6/6 (4, 55%), 8/8 (5, 58%), 10/10 (6, 53%), 8/6 (7, 52%), 10/8 (8, 51%)] as low-melting white solids on up to 10-g scales. The chiral tertiary phosphine [R f6(CH2)2][Rf8(CH2) 2][Rf10 (CH2)2]P (9) is similarly prepared from 7 and Rf10 CH=CH2 in the presence of VAZO (neat, 100C; 67%). The reaction of 5 and THFBH3 yields the phosphine borane 5BH3 (95%). Additions of triphosgene [(CCl3O)2CO] to 5 or Rf8(CH2) 2PH2 give [Rf8(CH2) 2]2PCl or Rf8(CH2) 2PCl2, which are characterized in situ. The CF 3C6F11/toluene partition coefficients of 4-9 increase with the number and lengths of the Rfn segments. 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

published proceedings

  • ADVANCED SYNTHESIS & CATALYSIS

author list (cited authors)

  • Emnet, C., Tuba, R., & Gladysz, J. A.

citation count

  • 5

complete list of authors

  • Emnet, Charlotte||Tuba, Róbert||Gladysz, JA

publication date

  • November 2005

publisher