Reactions of the perfluoroalkyltriazapentadiene Ph2N3C2(C3F7)2H with acids, bases, and water.
Treatment of the bis(perfluoroalkyl)triazapentadiene PhN=C(C(3)F(7))-N=C(C(3)F(7))-NHPh, 2, with bases affords salts of the conjugate base. Alkylation of the Na(+) salt with CH(3)I yields PhN=C(C(3)F(7))-N=C(C(3)F(7))-NMePh. The crystal structure of [Bu(4)N][Ph(2)N(3)C(2)(C(3)F(7))(2)] demonstrates a twisted, zigzag geometry for the anion in the solid state, but in solution, it is conformationally unstable. Both compounds are stable in aqueous methanol, but hydrolysis occurs under acidic conditions. Protonation with CF(3)SO(3)H acid occurs at the sp(2) nitrogen to give [PhN-(H) HC(C(3)F(7))-C(C(3)F(7))-NHPh][CF(3)SO(3)]. Heating 2 in CF(3)SO(3)H produces 2,4-bis(heptafluoropropyl)-1,3-quinazoline.
Siedle
A R
AR
3M Corporate Research Laboratories, St. Paul, Minnesota 55144, USA. arsiedle@mmm.com
Webb
Robert J
RJ
Brostrom
Myles
M
Chou
Shih-Hung
SH
Weil
David A
DA
Newmark
Richard A
RA
Behr
Fred E
FE
Young
Victor G
VG