Gompper, R., The Reactions

Gompper, R., The Reactions of Diazomethane with Heterocyclic Compounds, 2, 245. 

Yet another synthesis has been described by Prof. R. Gompper, involving the reaction of succinamide vith N,N-dimethylbenzamide diethylacetal (Scheme 11-5). 

Reactions of Acetylenecarboxylic Acids and Their Esters with Nitrogen-containing Heterocyclic Compounds R. M. Acheson, Adv. Heterocycl. Chem., 1963,1, 125-165. The Reactions of Diazomethane with Heterocyclic Compounds R. Gompper, Adv. Heterocycl. Chem., 1963, 2, 245-286. 

R. Gompper and H-U. Wagner, The Concept of Allopolarization. Effects of Substituents on the Reactions of Ambifunctional Anions , Angew. Chem. Internat. Edn., 1976, 15, 321. 

Continuous reactor. A soln. of 1,3,3-triethoxy-l-methoxypropane, formamide, and alcohol passed for 7 hrs. by means of an Ng-stream at 208° over mont-morillonite catalyst KSF between glass ring layers at such a rate that the reaction takes place during 3-6 min. pyrimidine (startg, m. f. 567). Y 72%. F. e. s. H. Bredereck, R. Gompper, and H. Herlinger, B. 91, 2832 (1958). 

No rearrangement occurs in the reaction with highly nucleophilic reactants, e. g. thiourea, whereas the rate of rearrangement increases with decreasingly nucleophilic reactants, e. g. thioacetamide. F. e., also oxazoles, s. H. Bredereck, R. Gompper, and F. Reich, B. 93, 723 (1960) thiazoles s. a. I. Steffan and B. Prijs, Helv. U, 1429 (1961). 

Cyclobutadiene itself is not stable at room temperature. Several derivatives with stabilizing groups have been prepared by the acid-catalyzed dimerization of alkjmes (R. Gompper, 1975). Less substituted cyclobutadienes could be obtained by photolytic reactions in solid matrix at low temperatures (G. Maier, 1973, 1974). 

---