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Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 5: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (10/20/06) from today (10/13/06). Grades will be administered as follows: 5
(exceptional effort), 4 (complete), 3 (incomplete or inadequate effort), 2 (poor effort), 0
(nonexistent). No late problem sets will be accepted.
1. Problem: The following one pot synthesis of semibulvalene has been reported (note reference
given below). Provide a plausible mechanism for this transformation.
N
N N
N
R
R
MeMe
MeMe
R
R
-2N2
heat
J. Sauer (Eur. J. Chem. 2002, 791).
2. Problem: In 1995 Miura and coworkers reported the remarkable reaction illustrated below (JOC,
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