Organic fluoronitrogens. IX. Oxidation-reduction reactions of tris(difluoramino)fluoromethane, tetrafluoroformamidine, and pentafluoroguandine

Organic polarography

“…Polarographic data for the reduction of methyl, ethyl, propyl, and butyl iodide at a dropping Ge electrode (29), for alicyclic chlorinated compounds (99), isomeric bromocitraconic and bromoesaconic acids (94), for the effect of alcohol on the reduction of CH3I and CjHgBr (332), disodium salt of 2',4',5',-7'-tetraiodofluorescem at pH 4.7 (62), alicyclic-halide derivatives of the type C6H5CH=CHCH2X and (C6H6)2C= CHCH2X (338), a series of homologous esters of the type RCHBrC02CH3 and BrCH2C02R (406), and for tris(difluoramino)fluoromethane, tetrafluoroformamidine, and pentafluoroguanidine (419) were reported. Cis and trans diethyl esters of dihalofumaric and dihalomaleic acids were studied polarographically (151,336).…”

Synthesis of Carboalkoxychloro- and Bromodiazirines

“…We have discovered that trichloroamidines 9 are reductively dechlorinated to the halodiazirines 1a − d with chloride or bromide ion under anhydrous conditions at room temperature (all yields are optimized). Chlorodiazirine 1a can be prepared in 45% yield by treatment of 9a with 5 equiv of tetrabutylammonium chloride (TBACl) in dry sulfolane (Scheme ).…”