Synthesis, crystal structure and hydrolysis of novel isomeric cage (P-C/P-O)-phosphoranes on the basis of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane and hexafluoroacetone

© The Royal Society of Chemistry 2016.The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P-C/P-O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P-C-isomer to P-O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P-O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P-C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol

Synthesis, crystal structure and hydrolysis of novel isomeric cage (P-C/P-O)-phosphoranes on the basis of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane and hexafluoroacetone

© The Royal Society of Chemistry 2016.The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P-C/P-O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P-C-isomer to P-O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P-O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P-C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol

Synthesis, crystal structure and hydrolysis of novel isomeric cage (P-C/P-O)-phosphoranes on the basis of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane and hexafluoroacetone

© The Royal Society of Chemistry 2016.The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P-C/P-O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P-C-isomer to P-O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P-O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P-C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol

Phosphonium salts with a dihydroxynaphthyl substituent: versatile synthesis and evaluation of antimicrobial activity

© 2017(1,4-Dihydroxynaphthalen-2-yl)phosphonium salts were obtained by reaction of P–H phosphonium salts with substituted 1,4-naphthoquinones. Some representatives of this series possess high activity against Gram-positive bacteria (Staphylococcus aureus ATCC 209p, Bacillus cereus ATCC 8035)

Phosphonium salts with a dihydroxynaphthyl substituent: versatile synthesis and evaluation of antimicrobial activity

© 2017(1,4-Dihydroxynaphthalen-2-yl)phosphonium salts were obtained by reaction of P–H phosphonium salts with substituted 1,4-naphthoquinones. Some representatives of this series possess high activity against Gram-positive bacteria (Staphylococcus aureus ATCC 209p, Bacillus cereus ATCC 8035)

Phosphonium salts with a dihydroxynaphthyl substituent: versatile synthesis and evaluation of antimicrobial activity

© 2017(1,4-Dihydroxynaphthalen-2-yl)phosphonium salts were obtained by reaction of P–H phosphonium salts with substituted 1,4-naphthoquinones. Some representatives of this series possess high activity against Gram-positive bacteria (Staphylococcus aureus ATCC 209p, Bacillus cereus ATCC 8035)