2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide

Micheletti Micheletti,Mazzacurati Mazzacurati,Telese Telese,Boga Boga

doi:10.3390/m1109

Abstract

2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide was synthesized (yield 50%) by a two-step procedure. The first step starts with a benzothiadiphosphole and bis-Grignard reagent, and the second step consists of adding the sodium salt of a derivative of cardanol. The structure of newly synthesized compound was elucidated based on 1H-NMR, 13C-NMR, 31P-NMR, IR, Electron Spray Ionization (ESI)–MS, Gas Chromatography-Mass Spectroscopy (GC–MS), and Electron Spray Ionization-High Resolution Mass Spectroscopy (ESI–HRMS).

Highlights

The synthesis of heterocyclic systems containing phosphorus is of considerable current interest, principally because they play a central role in coordination chemistry and homogeneous catalysis [1,2,3].In the past, we reported [4] that benzothiadiphosphole (1) can be obtained via a reaction between p-methylthioanisole, PCl3 and AlCl3, and it can be used as efficient phosphorus-donating reagent to obtain a plethora of phosphine derivatives [5,6,7,8]
The structure of the newly synthesized compound was elucidated based on IR, 1 H-NMR, 13 C-NMR, 31 P-NMR, electron spray ionization (ESI)–MS, Gas Chromatography-Mass Spectroscopy (GC–MS) and ESI–HRMS spectroscopy (All spectra are show in Supplementary Materials)
The structure of the newly synthesized compound was elucidated based on IR, 1H-NMR, 13CNMR, 31P-NMR, electron spray ionization (ESI)–MS, GC–MS and ESI–HRMS spectroscopy (All spectra are show in Supplementary Materials)

Summary

Introduction

The synthesis of heterocyclic systems containing phosphorus is of considerable current interest, principally because they play a central role in coordination chemistry and homogeneous catalysis [1,2,3].In the past, we reported [4] that benzothiadiphosphole (1) can be obtained via a reaction between p-methylthioanisole, PCl3 and AlCl3 , and it can be used as efficient phosphorus-donating reagent to obtain a plethora of phosphine derivatives [5,6,7,8]. The sodium salt of a hydrogenated derivative of cardanol (2) was added to the crude reaction mixture, and, after quenching with water, the final product 3 was obtained.

Results

Conclusion