
TY  - JOUR
A1  - Ung, AT 
A1  - Bishop, R 
A1  - Craig, DC 
A1  - Scudder, ML 
A1  - Yunus, J 
T1  - Ritter Reactions. VII. Diverse Reactivity of the 3-Azatricyclo[5.3.1.0<sup>4,9</sup>]-undec-2-ene System With Dimethyl Acetylenedicarboxylate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1992
VL  - 45
IS  - 3
SP  - 553
EP  - 565
KW  - 
UR  - https://doi.org/10.1071/CH9920553 
N2  - The imine functionality of the 3-azatricyclo[5.3.1.04,9]undec-2-ene derivatives (3a-c) reacts with dimethyl acetylenedicarboxylate to yield the lactam (5), the amino ester (6), and the oxopyrroline (7) respectively. Crystal structures of (6) [C31H34N2O5, Pca21, a 17.736(1), b  9.8412(4), c 15.584(1) Å , Z 4, R 0.032] and (7) [C33H36N2O6, Pca21, a 14.0610(8), b 9.6602(6), c 20.818(1) Å , 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. 
ER  -

