European Journal of Chemistry 2013, 4(4), 336-342 | doi: https://doi.org/10.5155/eurjchem.4.4.336-342.828 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity


Dmitry Murzin (1,*) , Vera Kolesova (2)

(1) Department of Chemical Engineering, Åbo Akademi University, Turku, 20500, Finland
(2) Department of Chemistry and Technology of Organic Synthesis, Faculty of Technology of Organic Substances and Pharmaceutical Chemistry, Mendeleev University of Chemical Technology, Moscow, 125047, Russia
(*) Corresponding Author

Received: 13 May 2013 | Revised: 11 Jun 2013 | Accepted: 14 Jun 2013 | Published: 31 Dec 2013 | Issue Date: December 2013

Abstract


A variety of 2-(N-alkoxy(thio)carbonyl alkyl(aryl)amino)-1,3,2-dioxaphospholanes and phosphorinanes were prepared from chlorodioxaphospholanes and phosphorinanes. Their structures were determined by IR, Mass and NMR spectroscopy. These compounds were employed in direct reactions with elemental sulphur and methylester of chloroacetic acid giving potentially physiologically active N-phosphorylated carbamates with P(O)-N and P(S)N bonds.

4_4_336_342

Keywords


Mass-spectra; Sulfur addition; Phosphorinanes; Arbuzov rearrangement; Chlorodioxaphospholanes; N-Phosphorylated carbamates

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.4.336-342.828

Links for Article


| | | | | | |

| | | | | | |

| |

Related Articles




Article Metrics

This Abstract was viewed 737 times | PDF Article downloaded 317 times


Citations

/


[1]. Kang Peng, Ming-Yuan Gao, Yu-Yan Yi, Jia Guo, Zhi-Bing Dong
Copper/Nickel-Catalyzed Selective C-S/S-S Bond Formation Starting from O -Alkyl Phenylcarbamothioates
European Journal of Organic Chemistry  2020(11), 1665, 2020
DOI: 10.1002/ejoc.201901884
/


References

[1]. Fahmy, M. A.; Fukuto, T. R.; Myers, R. O.; March, R. B. J. Agr. Food Chem. 1970, 18, 793-796.
http://dx.doi.org/10.1021/jf60171a014

[2]. Derkach, G. I.; Samarai, L. I.; Kirsanov, A. V. Russ. J. Gen. Chem. 1962, 32, 3761-3764.

[3]. Ivanova, Z. M.; Stukalo, E. N.; Tishchishina, A. S.; Derkach, G. I. Russ. J. Gen. Chem. 1970, 40, 1942-1948.

[4]. Pudovik, M. A.; Saakyan, G. M.; Khairullin, V. N.; Khailova, N. A.; Pudovik, A. N. Russ. Chem. Bull. 1999, 48, 806-807.
http://dx.doi.org/10.1007/BF02496276

[5]. Shokol, V. A.; Mikhailyuchenko, N. K.; Derkach, G. I. Russ. J. Gen. Chem. 1966, 36, 1442-1444.

[6]. Kolesova, V. A.; Aleshnikova, T. V.; Strepikheev, Y. A.; Arbuzova, M. V. Russ. J. Gen. Chem. 1985, 55, 2037-2039.

[7]. Conge, A.; Guimaraes, A. G.; Martin, J.; Nardin, R.; Robert, J. B. Org. Magn. Reson. 1974, 6, 629-635.
http://dx.doi.org/10.1002/mrc.1270061205

[8]. Dutton, F. E.; Gemrich, E. G.; Lee, B. L.; Nelson, S. J.; Parham, P. H.; Seaman, W. J. J. Agr. Food Chem. 1981, 29, 1114-1118.
http://dx.doi.org/10.1021/jf00108a003

[9]. Browne, J. E.; Driver, M. J.; Russel, J. C.; Sammes, P. G. J. Chem. Soc. Perkin Trans. I 2000, 653-657.

[10]. Lefort L.; Boogers, J. A. F.; Vries, A. H. M.; Vries, J. G. Org. Lett. 2004, 6, 1733-1735.
http://dx.doi.org/10.1021/ol049510e
PMid:15151401

[11]. Lefort L.; Boogers, J. A. F.; Vries, J. G.; Vries, A. H. M. Top. Catal. 2010, 53, 1081-1086.
http://dx.doi.org/10.1007/s11244-010-9536-2

[12]. Kawanobe, W.; Yamaguchi, K.; Rokicki, G.; Mei, S. K.; Yamazaki, N.; Nakahama, S. J. Polym. Sci. Pol. Chem. Ed. 1984, 22, 2371-2380.

[13]. Rokicki, G. Makrom. Chem. 1988, 189, 2513-2520.
http://dx.doi.org/10.1002/macp.1988.021891101

[14]. Rakhimov, A. I.; Pugacheva, E. A. Russ. J. Gen. Chem. 2008, 7, 50-52.

[15]. Antokhina, L. A.; Alimov, P. I. Bull. Acad. Sci. USSR. Div. Chem. Sci. 1971, 806-810.

How to cite


Murzin, D.; Kolesova, V. Eur. J. Chem. 2013, 4(4), 336-342. doi:10.5155/eurjchem.4.4.336-342.828
Murzin, D.; Kolesova, V. Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity. Eur. J. Chem. 2013, 4(4), 336-342. doi:10.5155/eurjchem.4.4.336-342.828
Murzin, D., & Kolesova, V. (2013). Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity. European Journal of Chemistry, 4(4), 336-342. doi:10.5155/eurjchem.4.4.336-342.828
Murzin, Dmitry, & Vera Kolesova. "Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity." European Journal of Chemistry [Online], 4.4 (2013): 336-342. Web. 28 Nov. 2020
Murzin, Dmitry, AND Kolesova, Vera. "Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.4.4.336-342.828

| | | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2013, 4(4), 336-342 | doi: https://doi.org/10.5155/eurjchem.4.4.336-342.828 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.