Phosphonyl Compounds

Convenient synthesis of phosphonohydrazines from arylamines

“…15 Simple phosphonohydrazines (without aryl groups) were synthesized by the reaction of monochlorophosphonate and hydrazine. 16–18 In a special case, 2,4-dinitrophenylated phosphonohydrazine has been isolated as a rearranged product from the reaction of bis(2,4-dinitrophenyl) phosphate with hydrazine. 19 This reaction therefore presented a convenient method for the preparation of phosphoryl derivatives of aromatic hydrazines.…”

Synthesis and Characterization of New Variously Substituted Allylic Phosphates

“…It is worth to note that the assignment of the stereochemistry of phosphates 3 was based on the E and Z isomer percentages in the starting aldehydes 1 and alcohols 2 since the integration of the two 31 P NMR signals for 3 gave approximately the same isomer percentages as those observed in the corresponding aldehydes 1 and alcohols 2. These were carefully measured from our own samples that were consistent with literature values [27][28][29] and compared with those obtained for phosphates 3 ( Table 2).…”

“…The products were characterized by IR, ( 1 H, 31 P, 19 F, and 13 C) NMR spectroscopy, and HRMS. In the IR spectra of phosphates 3, the disappearance of the OH band of starting alcohol and the appearance of a new absorbance in the range 1250-1300 cm −1 assigned to the P=O stretching vibration confirmed the formation of the new phosphates 3.…”

“…The lower reactivity of variously substituted allyl alcohols (2) compared to nonsubstituted allyl alcohols could also be due to their larger size, which required the use of DMAP in the preparation of allyl phosphates (3). The DMAP is believed to involve formation of a salt, where the pyridinium group has a better leaving ability than the chlorine atom of the chloridate [31].…”

“…In this work, we have converted these aldehydes into their corresponding allylic alcohols and reacted the latter with diethyl or diphenyl phosphorochloridates to produce new allylic phosphates. These were obtained in good yields and fully characterized by multinuclear ( 1 H, 13 C, 31…”