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2001
rearrangements
rearrangements
O 0140
Synthesis and Chemistry of Endoperoxides Derived from 3,416 - 064 Dihydroazulen-1(2H)-one: An Entry to Cyclopentane-Anellated
Tropone Derivatives. — Photo-oxygenation of azulene (III), accomplished
with TPP as sensitizer, affords peroxides (IV) and (V) with anti relation of the
methoxy group and the peroxide bridge, and a small amount of product (VI).
Both peroxides undergo rearrangement by thermolysis to give syn-bis(epoxides)
(VII) and (VIII). For the first time it is observed that thiourea acts as a base
instead of a reducing reagent in the reaction with these peroxides yielding
azulenones (IX) and (X). — (CELIK, MURAT; AKBULUT, NIHAT; BALCI,
METIN; Helv. Chim. Acta 83 (2000) 12, 3131-3138; Dep. Chem., Middle East
Tech. Univ., TR-06531 Ankara, Turk.; EN)
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