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Polyquinanes by [4 + 4] cycloaddition-transannular cyclization
T A Ader1, C A Champey, L V Kuznetsova
1Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400.
Organic Letters
|July 7, 2001
Abstract:
[reaction: see text] Photocycloaddition of 2-pyridones yields a rigid polycyclic product containing a 1,5-cyclooctadiene. The cis isomer, with the alkenes in close proximity, undergoes a transannular reaction when treated with chlorine to give a polyquinane product. The chlorination reaction involves migration of an amide nitrogen and forms a single isomer, generating eight stereogenic centers in two steps.