ISSN:
0009-2940
Keywords:
Pseudoazulenes
;
1,2,4,5-Tetrazines
;
[4 + 2] Cycloadditions, two-step
;
14π-Hetarenes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Pseudoazulenes as Dienophiles in the [4 + 2] Cycloaddition with Inverse Electron Demand[4 + 2] Cycloadditions of the pseudoazulenes 2, 6, 13, 18, and 22 to the extremely electron-deficient s-cis-fixed diazadiene system of 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine (1) are described. Probably according to a two-step mechanism the pseudoazulenes 2, 6, and 18 react with 1 to form the corresponding cycloadducts followed by elimination of nitrogen and oxidation to furnish the novel 14 systems 5, 12, and 21 in rather high yields. In contrast, with the cyclopenta[d]-pyridazines 13 and 22 the azines 17 and 26, respectively, are formed exclusively.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260927
