Synthesis of 4-(N,N-Dialkylamino)benzyltriphenylphosphonium Iodides from Hydroxymethyltriphenylphosphonium Iodide and N,N-Dialkylaniline

Synthesis and Properties of the Fluoromethylating Agent (Fluoromethyl)triphenylphosphonium Iodide

“…There are no significant fluorine–hydrogen interactions [shortest distance 2.51(3) Å]. In contrast, the crystal structure of the related triphenylphosphonium hydroxymethyl iodide (CH 2 F replaced by the bioisosteric CH 2 OH) is dominated by a –OH ··· I hydrogen bond; the interactions of I – to the CH 2 protons are in this case (as expected) weaker [CH ··· I distances of 3.0923(2) and 3.2070(2) Å] …”

Monofluorinated Nitrogen Containing Heterocycles: Synthesis, Characterization and Fluorine Effect

“…the CH•••I interaction corresponds to a distance of 3.092(2) Å. [23] The weak interactions are responsible that 7 decomposes at 252°C without melting and this occurs by approx. 50°C lower than the melting point of its methyl analogue (312°C).…”

1-Hydroxyalkylphosphonium Salts—Synthesis and Properties

“…Although such phosphonium salts were already described in the 1960s [ 15 , 16 , 17 ], their properties (apart from spectroscopic ones [ 18 , 19 ]) have not been studied in detail thus far. However, there have been some references to the synthesis of these compounds based on the three-component reaction of an aldehyde with phosphine in the presence of HX (aqueous or ethereal HBF 4 solution, concentrated hydrochloric acid, etc., Scheme 1 /Method A) [ 15 , 16 , 17 , 18 , 20 , 21 , 22 ] or the two-component reaction in the presence of complex triphenylphosphonium salts 5 ( Scheme 1 /Method B) [ 23 ]. Each time, they refer to individual examples—most often the synthesis of hydroxymethylphosphonium salts (R 1 = H, from paraformaldehyde or formalin).…”