Journal of the Chemical Society. Perkin transactions I p. 621 - 632 (1981)
Update date:2022-08-03
Topics:
Bloodworth, A.J.
Khan, Jamil A.
Loveitt, M.E.
The bis-mercuriated derivative (12) of 9,10-dioxabicyclo<3.3.2>decane has been prepared by peroxymercuriation of cis,cis-octa-1,5-diene, but substantial amounts of bicyclic ethers are also formed in the reaction.The bicyclic peroxides (4) and (5) have been obtained from (12) by reduction and brominolysis respectively. 8,9-Dioxabicyclo<5.2.1>decane (6) and the dibromo-derivative (7) have similarly been prepared by peroxymercuriation and demercuriation of cyclo-octa-1,4-diene.It is suggested that the isomeric purity of the peroxides and the concurrent formation of bicyclic ethers both result from equilibrium control of reversible (per)oxymercuriation-de(per)oxymercuriation.A low yield of the <3.2.1>-peroxide (8) has been obtained by peroxymercuriation and brominolysis of cyclohexa-1,4-diene, but attempts to prepare <2.2.1>-compounds from 5,5-disubstituted cyclopentadienes have been unsuccessful.
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