SYNTHESIS OF DIHYDROXYALKYLCYCLOPENTADIENES

Abstract

Alkylation of cyclopentadiene with dihydric alcohols of the C2-C4 series in the presence of an alkaline catalyst in a molar ratio of 1 : 2 in good yield have been carried out. The physico-chemical parameters of the synthesized products are determined. The structure of adducts is confirmed by modern physico-chemical methods of analysis.

References

[1] Volk B., Mezel T., Simig G. Raney nickel induced 3-alkylation of oxindole with alcohols and diols // Synlett. 2002. N 5. P. 595-597.
[2] Yan T. Iron catalyzed alkylation and N-heterocyclization of amines with alcohols // Abstr. оf ISGC, Groningen, Holland, 16-19 may 2016. P. 42.
[3] Ting Y., Lan-Jun Q., Dong M. N-alkylation of sulfonamides with alcohols by Tf2O // Bull. Chem. Soc. Japan, 2015. N 88. P. 610-612.
[4] Pat. US 4260852A, 1981 Alkylation of 2,6-di-tertalkylphehols with alkanediols Parker D., Kline R.
[5] Tateyama K., Hiroki M., Kenji W. Selective N-alkylation of primary amines with diols promoted by metal oxide-supported iridium catalysts // Proceedings of Annual/Fall Meeting of the Japan Petroleum Institute. 2012. P. 127.
[6] Car-Kobeci G., Statfard P., Whittlesey M. N-alkylation of phenethylamine and tryptamine // Bioorganic and Medicinal Chemistry Letters. 2005. Vol. 15, N 3. P. 535-537.
[7] Yang Q., Wang Q., Zhengkun Y. Substitution of alcohols by N-nucleophiles via transition metal-catalyzed dehydrogenation // Chem. Soc. Rev. 2015. Vol. 44. P. 2305-2310.
[8] Yasushi O., Yasutaka I. Iridium-catalyzed reactions involving transfer hydrogenation, addition, N-heterocyclization and alkylation using alcohols and diols as key substrates // Synlett. 2011. N 1. P. 30-51.
[9] Shan S., Xiaoke X., Dang T. Benzimidazolin-2-ylidene N-heterocyclic carbene complexes of ruthenium as a simple catalyst for the N-alkylation of amines using alcohols and diols // RSC Advances. 2015. N 6. P. 239-241.
[10] Malnar A., Tarak B., Bucsi I. Alkylation of aromatics with diols in superacidic media // Topics in Catalysis. 1998. Vol. 6, N 1-4. P. 9-16.
[11] Yan T., Feringa B. Iron catalyzed direct alkylation of amines with alcohols // Nature Communications. 2014. N 5. P. 5602-5607.
[12] Kawahara R., Fujita K., Yamaguchi R. Multialkylation of aqueous ammonia with alcohols catalyzed by water-soluble CpIr-ammine complexes // J. Amer. Chem. Soc. 2010. Vol. 132, N 43. P. 15108-15111.
[13] 1Jian J., MacMillan D. Alcohols as alkylating agents in heteroarene C-H functionalization // Nature. 2015. Vol. 525. P. 87-90.
[14] Petersen L. Iridium- and ruthenium-catalyzed N-alkylation of amines with alcohols and amines // PhD thesis, Technical University of Denmark. 2012. 137 p.
[15] Gasanov A.G., Azizov A.G., Memmedova A.M., Ayyubov I.G. Synthesis of perspective hydrocarbons for synthetic lubricants with a high viscosity characteristic // International Journal of Emerging Engineering Research and Technology (India). 2015. Vol. 3, N 11. P. 92-96.
[16] Gasanov A.G., Azizov A.G., Memmedova A.M., Ayyubov I.G. Synthesis and characterization of di-n.hexylcyclopentane // International Journal of Scientific Engineering and Applied Science (India). 2016. Vol. 2, N 2. P. 335-337.