Cycloaddition-Fragmentation as a Route to Bicyclic Ring Systems. Use of the Intermolecular Diyl Trapping Reaction.
A route to bicyclo[n.3.0] ring systems (n = 5-7) has been devised. Key transformations include an intermolecular diyl trapping reaction (1 + 3 --> 4), and fragmentation of the resulting tricyclic cycloadduct 4 (4 --> 5). A variety of diylophiles were examined, including electron deficient (6, 7, 21, 29, 30, 31), electron rich (8), and push-pull cycloalkenes (9, 10, 19, 20).
Leonetti
Joseph A.
JA
Department of Chemistry, University of California-Santa Barbara, Santa Barbara, California 93106.
Gross
Tim
T
Little
R. Daniel
RD