Synthesis and Properties of Condensed Ureidomethyl Phosphonium Salts

Frank, Arlen W.

doi:10.1080/03086648108077497

Cited by 12 publications

(3 citation statements)

References 5 publications

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“…The chloromethyl derivative lOa exhibits a characteristic CH2 deformation band at 1400 cm-' [55]. ELECTRON [ 119] and for the polymeric urea derivatives 30 and 31 [43]. The P2p and Chp peak positions are similar to those reported for other quaternary phosphonium salts.…”

Section: Reactionssupporting

confidence: 54%

“…The dissociation of THPC to THP and formaldehyde is repressed by acids such as hydrochloric acid (Equation 2, common ion effect) [45,52,66], but on prolonged heating with constantly boiling hydrochloric acid at 110°, THPC rearranges to bis(hydroxymethyl)methylphosphine oxide (43) [42]:…”

Section: Reactions In Nonhydroxylic Mediamentioning

confidence: 99%

“…The tetrakis-(hydroxymethyl)phosphonium salts 1 exhibit PCH2 doublets in the 4.6 to 4.8 ppm region having coupling constants (J~H) of about 1.5-2.5 Hz, owing to coupling with phosphorus [44,56]. Substitution with carbamate or urea residues moves the chemical shifts upfield to 3.8-4.6 ppm and increases the coupling constant to 3.0-4.0 Hz for the acyclic compounds and to 6.5-9.0 Hz for the cyclic compounds [43,44,50]. Coupling of CH2 to NH of the order of 5 Hz is observed in those compounds that are sufficiently soluble in nonaqueous solvents [50].…”

Section: Reactionsmentioning

confidence: 99%

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Chemistry of Hydroxymethyl Phosphorus Compounds

Frank

Daigle

Vail

1982

Textile Research Journal

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The chemistry of the hydroxymethyl phosphonium salts and their derivatives is reviewed, with major emphasis on reactions in which the quaternary structure of the phosphonium salts is preserved.The subject matter covered in this review is restricted to phosphonium salts that are of interest to textile chemists as flame retardants for cotton. Formally, these compounds are derived from tetramethylphosphonium chloride, Me4PCl, or its equivalent (CH3)4P'Cl-, by substituting a single OR, NR2, or halogen substituent, where R = H, alkyl, aryl, acyl, alkoxycarbonyl, or aminocarbonyl group or combination thereof, for a hydrogen atom in each and every methyl group, or by substituting another anion for the chloride anion. There are many phosphonium salts that do not fall into this classification. For these, the reader should consult a textbook on organo-4 Names of companies or commercial products are given solely for the purpose of providing specific information. Their mention does not imply recommendation or endorsement by the U.S. Department of Agriculture over others not mentioned.

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Section: Reactionssupporting

confidence: 54%