Addition of alcohols to 4-methylene-1,3-dioxolanes

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Abstract

The addition of alcohols to 2-methylene-1,4-dioxaspiro[4.5]decane under the conditions of CF3CO2H catalysis occurs with the selective formation of the corresponding alkoxy derivatives. The conditions that ensure the preparative isolation of target compounds in 63-94% yields are determined, and the relative activity of alcohols in the addition reaction at the exocyclic double bond of substrates is determined.

About the authors

S. A Sokov

Ufa State Petroleum Technological University

Yu. G. Borisova

Ufa State Petroleum Technological University

Email: yulianna_borisova@mail.ru

G. Z Raskil'dina

Ufa State Petroleum Technological University

S. S Zlotsky

Ufa State Petroleum Technological University

A. A Golovanov

Ufa State Petroleum Technological University

References

  1. Sudarsanam P., Mallesham B., Prasad A.N., Reddy P.S., Reddy B.M. // Fuel Process. Technol. 2013. Vol. 106. P. 539. doi: 10.1016/j.fuproc.2012.09.025
  2. Kumar K., Pathak S., Upadhyayula S. // Renew. Energy.2021. Vol. 167. P. 282. doi: 10.1016/j.renene.2020.11.084
  3. Опарина Л.А., Высоцкая О.В., Степанов А.В., Гусарова Н.К., Трофимов Б.А. // ЖОрХ. 2012. Т. 48. № 9. С. 1166
  4. Oparina L.A., Vysotskaya O.V., Stepanov A.V., Gusarova N.K., Trofimov B.A.// Russ. J. Org. Chem. 2012. Vol. 48. N 9. P. 1162. doi: 10.1134/S1070428012090023
  5. Moity L., Benazzouz A., Molinier V., Nardello-Rataj V., Elmkaddem M.K., de Caro P., Thiébaud-Roux S., Gerbaud V., Marione P., Aubry J.-M. // Green Chem. 2015. Vol. 17. N 3. P. 1779. doi: 10.1039/C4GC02377C
  6. Раскильдина Г.З., Кузьмина У.Ш., Джумаев Ш.Ш., Борисова Ю.Г., Ишметова Д.В., Вахитова Ю.В., Злотский С.С. // Изв. АН. Сер. хим. 2021. Т. 70. № 3. С. 475
  7. Raskil'dina G.Z., Kuzmina U.Sh., Dzhumaev Sh.Sh., Borisova Yu.G., Ishmetova D.V., Vakhitova Yu.V., Zlotskii S.S. // Russ. Chem. Bull. 2021. Vol. 70. N 3. P. 475. doi: 10.1007/s11172-021-3111-9
  8. Meng S.-S., Liang Y., Cao K.-S., Zou L., Lin X.-B., Yang H., Houk K.N., Zheng W.-H. // J. Am. Chem. Soc. 2014. Vol. 136. N 35. P. 12249. doi: 10.1021/ja507332x
  9. Johnsson R., Ohlin M., Ellervik U. // J. Org. Chem. 2010. Vol. 75. N 23. P. 8003. doi: 10.1021/jo101184d
  10. Опарина Л.А., Колыванов Н.А., Ганина А.А., Дьячкова С.Г. // Нефтехимия. 2020. Т. 60. № 1. С. 148
  11. Oparina L.A., Kolyvanov N.A., Ganina A.A., D'yachkova S.G. // Petrol. Chem. 2020. Vol. 60. N 1. P. 134. doi: 10.1134/S0965544120010107
  12. Frauenrath H., Runsink J. // J. Org. Chem. 1988. Vol. 53. N 9. P. 1860. doi: 10.1021/jo00244a004.
  13. Orth H. // Angew. Chem. 1952. Vol. 64. N 19-20. P. 544. doi: 10.1002/ange.19520641908
  14. Brandsma L. Synthesis of Acetylenes, Allenes and Cumulenes. Methods and Techniques. Amsterdam
  15. Tokyo: Elsevier, 2004. P. 123.

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