SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE

Jutzi P, Mix A (1992)
CHEMISCHE BERICHTE-RECUEIL 125(4): 951-954.

Journal Article | Published | English

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Abstract
Pentamethylcyclopentadienyl bromide 1 reacts with silver tetrafluoroborate with abstraction of the halide ion to form pentamethylcyclopentadienylium tetrafluoroborate (2). The 4-pi-antiaromatic cation in 2 can be trapped with different nucleophiles. Thus, 2 reacts with methanol to give 5-methoxy-1,2,3,4,5-pentamethyl-1,3-cyclopentadiene (4). In the presence of methylamine, dimethylamine, or diethylamine, the corresponding pentamethylcyclopentadienyl-substituted amines 5, 6, and 9 are formed. Trapping of 1 with pyridine or dimethyl sulfide leads to the ionic compounds 7 and 8, respectively. The reaction of 2 with sterically crowded amines leads to tetramethylfulvene (3).
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Jutzi P, Mix A. SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE. CHEMISCHE BERICHTE-RECUEIL. 1992;125(4):951-954.
Jutzi, P., & Mix, A. (1992). SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE. CHEMISCHE BERICHTE-RECUEIL, 125(4), 951-954.
Jutzi, P., and Mix, A. (1992). SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE. CHEMISCHE BERICHTE-RECUEIL 125, 951-954.
Jutzi, P., & Mix, A., 1992. SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE. CHEMISCHE BERICHTE-RECUEIL, 125(4), p 951-954.
P. Jutzi and A. Mix, “SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE”, CHEMISCHE BERICHTE-RECUEIL, vol. 125, 1992, pp. 951-954.
Jutzi, P., Mix, A.: SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE. CHEMISCHE BERICHTE-RECUEIL. 125, 951-954 (1992).
Jutzi, Peter, and Mix, Andreas. “SYNTHESES WITH THE REAGENT PENTAMETHYLCYCLOPENTADIENYL BROMIDE/SILVER TETRAFLUOROBORATE - THE PENTAMETHYLCYCLOPENTADIENYL CATION AS REACTIVE INTERMEDIATE”. CHEMISCHE BERICHTE-RECUEIL 125.4 (1992): 951-954.
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