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Trimetaphosphate (TriMP, [P 3 O 9 ] 3- ) reacts with PyAOP ([(H 8 C 4 N) 3 PON 4 C 5 H 3 ][PF 6 ]) to yield an activated TriMP, [P 3 O 9 P(NC 4 H 8 ) 3 ] - (1), incorporating a phosphonium moiety. Anion 1 is isolated as its bis(triphenylphosphine)iminium (PPN) salt in 70% yield and phosphorylates nucleophiles with elimination of phosphoramide OP(NC 4 H 8 ) 3 . Treatment of 1 with amines HNR 1 R 2 generates [P 3 O 8 NR 1 R 2 ] 2- (2a: R 1 = R 2 = Et; 2b: R 1 = H, R 2 =  Bu) in greater than 70% yield as mixed PPN and alkyl ammonium salts. Treatment of 1 with primary alcohols in the presence of a tertiary amine base results in salts of intact TriMP alkyl esters [P 3 O 9 R] 2- (3a: R = Me; 3b: R = Et) in greater than 60% isolated yield. Reaction of 1 with [PPN][H 2 PO 4 ] provides orthophosphoryl TriMP (4, [P 4 O 12 H 2 ] 2- ) in 40% yield as the PPN salt. Treatment of 1 with Wittig reagent H 2 CPPh 3 (4 equiv) provides phosphorus ylide [P 3 O 8 CHPPh 3 ] 2- (5) in 61% yield as a mixed salt. Ylide 5 reacts with water to provide [P 3 O 8 Me] 2- (6) and with aldehydes to give olefins [P 3 O 8 CHCHR] 2- (7a: R = H; 7b: R = 4-C 6 H 4 Br), products in which one TriMP oxygen is replaced by a phosphonate P-C linkage. Treatment of intact TriMP derivatives 2a, 2b, 3a, and 7a with aqueous tetrabutylammonium hydroxide results in ring opening to linear triphosphate derivatives. X-ray crystal structures are provided for salts of 1, 2a, 3a, and 4.

Functionalization of Intact Trimetaphosphate: A Triphosphorylating Reagent for C, N, and O Nucleophiles