ChemInform Abstract: Phosphorylation of 1‐Morpholinocyclohexene and ‐cyanopentene. Convenient Synthesis of a Phosphorylated Cyclohexanone and Cyclopentanone Derivatives.

Abstract

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Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes

“…31 P­{ 1 H} NMR (121 MHz, DMSO- d 6 ): δ 32.83 and 32.07 (both isomers). NMR spectra are in agreement with literature data . HRMS: m / z [M + H] + calcd for [C 18 H 21 NO 2 P] + , 314.1304; found, 314.1302.…”

“…8 Hz,4 CH),128.6 (d,J = 12.3 Hz,4 CH), 61.7 (CH 2 ), 28.7 (d, J = 64.7 Hz, CH 2 ), 14.1 (CH 3 ). 31 2-(Diphenylphosphoryl)propanal Oxime (5g). The compound was prepared according to a general procedure from 101 mg of diphenylphosphine oxide (0.5 mmol) and 233 mg of enamine 4g (1.0 mmol).…”

Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel α‐(Diphenylphosphoryl)‐ and α‐(Diphenylphosphorothioyl)cycloalkanone Oximes

“…The starting α-(diphenylphosphoryl)-and α-(diphenylphosphorothioyl)cycloalkanones 1 were easily prepared from the reaction of a cyclic enamine with P-chlorodiphenylphosphine in the presence of triethylamine, followed by oxidation or sulfurization and hydrolytic work-up, according to the reported procedure. [32][33][34] Reaction of compounds 1 with hydroxylamine hydrochloride, conducted in refluxing ethanol for 24 h in the presence of an equimolar quantity of potassium hydroxide, led to the desired α-(diphenylphosphoryl)-and α-(diphenylphosphorothioyl)cycloalkanone oximes 2. The isolated yield of the reaction ranges from 81 to 89% (Table 1).…”

Direct Regio- and Diastereoselective Diphosphonylation of Cyclic Enamines: One-Pot Synthesis of α,α′-Bis(diphenylphosphoryl)- and α,α′-Bis(diphenylphosphorothioyl)cycloalkanones

“…Initially, the reaction was tested with one equivalent Ph 2 PCl and 1.1 equivalents Et 3 N in different solvents, in order to improve the experimental protocol for the formation of the monophosphonylated products 22,23 and to ascertain if the desired diphosphonylated compounds could be detected in these conditions. The reaction provided mainly the monophosphonylated product 3a with trace amounts of the α,α′-bis(diphenylphosphoryl)cyclohexanone (2a, Table 1, entries 1-6).…”

“…[11][12][13][14][15][16] Some of their fluorescent complexes with lanthanum-group metals are also used as light-emitting components in organic light-emitting diodes. 17 Within our ongoing studies on the reactivity and potential synthetic applications of imines and enamines [18][19][20][21] and inspired by the reaction of enamines with chlorophosphines which leads to α-phosphonylcycloalkanones, 22,23 we anticipated that treatment of cyclic enamines with excess P-chlorodiphenylphosphine, followed by oxidation or sulfurization and hydrolytic workup, would allow a straightforward approach to unprecedented symmetrical α,α′bis(diphenylphosphoryl)-and α,α′-bis(diphenylphosphorothioyl)cycloalkanones. Being tridentate ligands, these compounds might show enhanced complexing properties with regard to their α-phosphonylketone homologues.…”