Efficient syntheses of fluorous primary phosphines that do not require PH3 Academic Article

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, 160C) 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.

authors

• Gladysz, John

published proceedings

• SYNTHESIS-STUTTGART

author list (cited authors)

• Emnet, C., & Gladysz, J. A.

citation count

• 2

complete list of authors

• Emnet, C||Gladysz, JA

publication date

• April 2005

publisher

• Thieme  Publisher

keywords

• Arbuzov Reaction
• Fluorous
• Partition Coefficients
• Phosphines
• Phosphonates

Digital Object Identifier (DOI)

• 10.1055/s-2005-861815

start page

• 1012

end page

• 1018

volume

• 2005

issue

• 6

URL

• http%3A%2F%2Fdx.doi.org%2F10.1055%2Fs-2005-861815