128102-19-2Relevant academic research and scientific papers
Ritter Reactions. VII. Diverse Reactivity of the 3-Azatricyclo4,9>undec-2-ene System with Dimethyl Acetylenedicarboxylate
Ung, Alison T.,Bishop, Roger,Craig, Donald C.,Scudder, Marcia L.,Yunus, Jamilah
, p. 553 - 565 (2007/10/02)
The imine functionality of the 3-azatricyclo4,9>undec-2-ene derivatives (3a-c) reacts with dimethyl acetylenedicarboxylate to yield the lactam (5), the amino ester (6), and the oxopyrrolidine (7) respectively.Crystal structures of (6) 1, a 17.736(1), b 9.8412(4), c 15.584(1) Angstroem, Z 4, R 0.032> and (7) 1, a 14.0610(8), b 9.6602(6), c 20.818(1) Angstroem, Z 4, R 0.038> were determined.These widely differing modes of reaction result from the nature of the imine C2 substituent present in the starting material (3).Tentative mechanistic explanations are presented.
Ritter Reactions. V. Further Investigation of the 3-Azatricyclo4,9>undec-2-ene System
Bong, Ivy C.C.,Ung, Alison T.,Craig, Donald C.,Scudder, Marcia L.,Bishop, Roger
, p. 1929 - 1937 (2007/10/02)
2,6-Dimethylenebicyclononane (1) and acetonitrile react under Ritter reaction conditions to produce exo-11-acetamido-2,4,endo-11-trimethyl-3-azatricyclo4,9>undec-2-ene (2) monohydrate whose crystal structure 1, a 8.213(3), b 10.841(1), c 8.234(2) Angstroem, β 95.57(2) deg, Z 2> was determined with a final R 0.036.The diene (1) reacts similarly with benzonitrile to produce the phenyl-substituted analogue (3).In contrast, the reaction of (1) and benzyl cyanide yields a different type of product, 2-benzoyl-4,endo-11-dimethyl-exo-11-phenylacetamido-3-azatricyclo4,9>undec-2-ene (5a), where one of the two nitrile-derived groups has undergone spontaneous oxidation during the one-flask preparation. p-Bromo- and p-chloro-benzyl cyanides behave in a similar manner yielding the adducts (5b,c) respectively.
