Influence of the quaternary ammonium salt on the addition of alpha-cyanocarbanions to mesityl oxide, methyl crotonate and cinnamate, and methyl sorbate under phase transfer catalysis

1,4-addition of nitrile 1a to mesityl oxide 2 giving 7a has been easily achieved under PTC liquid-liquid conditions using tetrabutylamnmonium hydrogen sulfate as catalyst, the quaternary ammonium salt/1a molar ratio being 0.37. In the same way, 1,4-addition of 1a-b to methyl crotonate 3 and methyl c...

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Bibliographic Details
Published inPolish journal of chemistry Vol. 70; no. 3; pp. 325 - 333
Main Authors RouxSchmitt, MC, Croisat, D, SeydenPenne, J, Wartski, L, Cossentini, M
Format Journal Article
LanguageEnglish
Published WARSAW POLISH CHEMICAL SOCIETY 01.03.1996
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MICHAEL REACTION
REAGENTS
ACIDS
mesityl oxide
methyl crotonate
PTC liquid-liquid conditions
methyl sorbate
tetrabutylammonium hydrogen sulfate
1,4-addition
1,6-addition
CHEMISTRY
methyl cinnamate
ARYLACETONITRILES
CONJUGATE ADDITION
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Summary:1,4-addition of nitrile 1a to mesityl oxide 2 giving 7a has been easily achieved under PTC liquid-liquid conditions using tetrabutylamnmonium hydrogen sulfate as catalyst, the quaternary ammonium salt/1a molar ratio being 0.37. In the same way, 1,4-addition of 1a-b to methyl crotonate 3 and methyl cinnamate 4 could be also performed leading to 8a-b and 9a-b, respectively. In contrast, these mild conditions gave mixtures of 1,4-adducts 12a-b and 1,6 adducts 10a-b and 11a with methyl sorbate 5. The lithiated derivatives of 1a-b gave exclusively the 1,6-adducts 10a-b under aprotic conditions.
ISSN:0137-5083