Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol

Antero Laitinen (Corresponding Author), Yoshihiro Takebayashi, Irene Kylanlahti, Jari Yli-Kauhaluoma, Tsutomu Sugeta, Katsuto Otake

Research output: Contribution to journalArticleScientificpeer-review

12 Citations (Scopus)

Abstract

Ene reaction of allylbenzene and N-methylmaleimide was studied in water and ethanol solvents at subcritical temperatures (220–310 °C). Subcritical water was inappropriate for this reaction, because it rapidly hydrolyzed N-methylmaleimide. Subcritical ethanol was found to be a very promising solvent. The highest ene product yield in ethanol reached 40% in 480 min, and the highest trans-selectivity was 92%. The yields in pure ethanol were comparable to those in 1,2,4-trichlorobenzene with 10% hydroquinone added as a polymerization inhibitor. Addition of hydroquinone had a negligible effect on the yield in ethanol, suggesting that the solvent ethanol itself acts as an inhibitor of the side reactions. It is also expected that the polar environment and the high vapor pressure of ethanol favored pericyclic association between the apolar starting compounds.
Original languageEnglish
Pages (from-to)49 - 52
Number of pages4
JournalGreen Chemistry
Volume6
Issue number1
DOIs
Publication statusPublished - 2004
MoE publication typeA1 Journal article-refereed

Fingerprint

ethanol
Ethanol
Water
water
inhibitor
allylbenzene
N-methylmaleimide
Vapor pressure
vapor pressure
polymerization
Polymerization
Association reactions
temperature
Temperature

Keywords

  • allylbenzene
  • Ene reaction
  • ethanol

Cite this

Laitinen, A., Takebayashi, Y., Kylanlahti, I., Yli-Kauhaluoma, J., Sugeta, T., & Otake, K. (2004). Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol. Green Chemistry, 6(1), 49 - 52. https://doi.org/10.1039/b304959k
Laitinen, Antero ; Takebayashi, Yoshihiro ; Kylanlahti, Irene ; Yli-Kauhaluoma, Jari ; Sugeta, Tsutomu ; Otake, Katsuto. / Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol. In: Green Chemistry. 2004 ; Vol. 6, No. 1. pp. 49 - 52.
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Laitinen, A, Takebayashi, Y, Kylanlahti, I, Yli-Kauhaluoma, J, Sugeta, T & Otake, K 2004, 'Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol', Green Chemistry, vol. 6, no. 1, pp. 49 - 52. https://doi.org/10.1039/b304959k

Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol. / Laitinen, Antero (Corresponding Author); Takebayashi, Yoshihiro; Kylanlahti, Irene; Yli-Kauhaluoma, Jari; Sugeta, Tsutomu; Otake, Katsuto.

In: Green Chemistry, Vol. 6, No. 1, 2004, p. 49 - 52.

Research output: Contribution to journalArticleScientificpeer-review

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T1 - Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol

AU - Laitinen, Antero

AU - Takebayashi, Yoshihiro

AU - Kylanlahti, Irene

AU - Yli-Kauhaluoma, Jari

AU - Sugeta, Tsutomu

AU - Otake, Katsuto

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AB - Ene reaction of allylbenzene and N-methylmaleimide was studied in water and ethanol solvents at subcritical temperatures (220–310 °C). Subcritical water was inappropriate for this reaction, because it rapidly hydrolyzed N-methylmaleimide. Subcritical ethanol was found to be a very promising solvent. The highest ene product yield in ethanol reached 40% in 480 min, and the highest trans-selectivity was 92%. The yields in pure ethanol were comparable to those in 1,2,4-trichlorobenzene with 10% hydroquinone added as a polymerization inhibitor. Addition of hydroquinone had a negligible effect on the yield in ethanol, suggesting that the solvent ethanol itself acts as an inhibitor of the side reactions. It is also expected that the polar environment and the high vapor pressure of ethanol favored pericyclic association between the apolar starting compounds.

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KW - Ene reaction

KW - ethanol

U2 - 10.1039/b304959k

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