P-NITROBENZYL FLUORIDE

Evaporation to dryness under reduced pressure gives 20.9-22.1 g. (90-95%) of crude product. Purification by recrystallization from 500 ml. of pentane yields 15.5 g. (67%) of p-nitrobenzyl fluoride as colorless needle-shaped crystals, m.p. 36-37 (Note 2). 

Synthetic applications of organosulfur reagents are expanding rapidly. Stable sulfuranes are included for the first time in BIS[2,-2,2-TRIPLUORO-l-PHENYL-l-(TRIFLUOROMETHYL)ETHOXY] diphenyl SULFURANE and DIETHYLAMINOSULFUR TRI-FLUORIDE. The latter is used to transform an alcohol to a fluoride in p-NITROBENZYL FLUORIDE. The direct homologation of a ketone to a nitrile by use of p-TOLYLSULFONYLMETHYL ISOCYANIDE is illustrated in 2-ADAMANTANECARBONITRILE. Reagents with... 

Nickel, dichloro [ethylenebis(dimethyl-phosphine)], 58, 133 Nickel, dichloro[ethj lenebis(diphenyl-phosphine)], 58,133 [Ni (-)-diop Cl2 ], (-)-diop=2,3-0-iso-propylidene-2,3-dihydroxy-l,4-bis(di-phenylphosphino)butane, 58, 133 Nickel, dichloro [ trimethylenebis(diphenyl-phosphine)], 58,133 NITRILES, alkylation of, 55, 91 NITRILES FROM KETONES, 58, 101 NITRILES, a vinyl, 55, 99, 101 p-Nitrobenzenesulfonyl cyanide, 57, 89 p-Nitrobenzyl alcohol, 57, 72 p-NITROBENZYL FLUORIDE, 57, 72 Nitro compounds, 56, 36 Nitronates, 56, 36... 

Diethylaminosulfur trifluoride, 6, 183-184. Detailed directions are available for preparation of this fluorination reagent and for its reaction with p-nitrobenzyl alcohol to form p-nitrobenzyl fluoride (67% yield). ... 

Nitrobenzenesulfenyl chloride, 360 p-Nitrobenzyl fluoride, 156 N-Nitrocollidinium tetrafluoroborate, 361... 

A photoactive peptide with potential for photoaflinity studies, containing L-p-azidotetrafluorophenylalanine, has been synthesized by the solid-phase Fmoc technique. 3-Azido-5-nitrobenzyl fluoride has been labelled with F in 30-50% yield, and was photochemically attached to a hexylamine-modified, 15-base, single stranded DNA aptamer, with up to 20% radiolabelling efficiency. This is claimed to demonstrate the feasibility of photolabelling oligonucleotide molecules with the positron-emitting F for PET applications. 

---