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

Antero Laitinen; Yoshihiro Takebayashi; Irene Kylanlahti; Jari Yli-Kauhaluoma; Tsutomu Sugeta; Katsuto Otake

doi:10.1039/b304959k

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 journal › Article › Scientific › peer-review

14 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 language	English
Pages (from-to)	49 - 52
Number of pages	4
Journal	Green Chemistry
Volume	6
Issue number	1
DOIs	https://doi.org/10.1039/b304959k
Publication status	Published - 2004
MoE publication type	A1 Journal article-refereed

Keywords

allylbenzene
Ene reaction
ethanol

Access to Document

10.1039/b304959k

Cite this

@article{da5faf5356b448b0b4ddda1fb3cbc60b,

title = "Ene reaction of allylbenzene and N-methylmaleimide in subcritical water and ethanol",

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.",

keywords = "allylbenzene, Ene reaction, ethanol",

author = "Antero Laitinen and Yoshihiro Takebayashi and Irene Kylanlahti and Jari Yli-Kauhaluoma and Tsutomu Sugeta and Katsuto Otake",

year = "2004",

doi = "10.1039/b304959k",

language = "English",

volume = "6",

pages = "49 -- 52",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "Royal Society of Chemistry RSC",

number = "1",

}

TY - JOUR

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

PY - 2004

Y1 - 2004

N2 - 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.

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.

KW - allylbenzene

KW - Ene reaction

KW - ethanol

U2 - 10.1039/b304959k

DO - 10.1039/b304959k

M3 - Article

SN - 1463-9262

VL - 6

SP - 49

EP - 52

JO - Green Chemistry

JF - Green Chemistry

IS - 1

ER -

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this