Kniep, Carina Sofia; Boese, Roland; Sustmann, Reiner:
Cycloaddition of 1,4-dimethyl-2,3-dimethylenehexahydropyrazine to electron deficient alkenes.
2000
In: Tetrahedron (Tetrahedron), Jg. 56 (2000), Heft 25, S. 4157 - 4162
Artikel/Aufsatz in Zeitschrift2000Chemie
Titel:
Cycloaddition of 1,4-dimethyl-2,3-dimethylenehexahydropyrazine to electron deficient alkenes.
Autor(in):
Kniep, Carina Sofia; Boese, RolandLSF; Sustmann, Reiner
Erscheinungsjahr
2000

Abstract:

The mechanism of cycloaddn. of 1,4-dimethyl-2,3-dimethylenehexahydropyrazine to moderately and highly electrophilic alkenes is probed by stereochem. studies. Retention of configuration for the E/Z-isomeric alkenes fumaro- and maleonitrile and loss of stereospecificity for di-Me dicyanofumarate and di-Me dicyanomaleate show that the mechanism of cycloaddn. (concerted or stepwise) depends on the gap between nucleophilic and electrophilic character of the reaction partners. The behavior of 1,4-dimethyl-2,3-dimethylenenehexahydropyrazine follows that of other amino-substituted dienes.