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The Behaviour of (1α,2α,5α,6α)-3,4-Bis(trimethylsilyloxy)tricyclo2,5>nona-3,7-diene on Treatment with Oxidative Reagents
Ried, Walter,Bellinger, Oswald
, p. 1778 - 1784 (2007/10/02)
(1α,2α,5α,6α)-3,4-Bis(trimethylsilyloxy)tricyclo2,5>nona-3,7-diene (1) is treated with different oxidative reagents.The reaction with halogens (Br2, Cl2) primarily yields the cyclobutanedione 2 which adds a second mole of halogen at the olefinic double bond.The adduct 3 is stabilized by forming 4a with an intramolecular ether bridge.Addition of chlorine to 2 directly yields 4b. - Reaction of 1 with DMSO/Ac2O or Cu(II) acetate in acetic acid causes an oxidative dimerization to yield 5 or 6, respectively.In the case of Cu(II) acetate the anhydride 7 is obtained as a second product.
