140844-49-1Relevant 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.
