Abstract
AbstractThe preparation, isolation, structure determination, and some reactions of the two stereoisomers of 2‐iodo‐9‐oxabicyclo[4.2.1]nonane (9 and 10) and of 2‐iodo‐9‐oxabicyclo[3.3.1]‐nonane (11 and 12), respectively, are described.Iodine cleavage of the [4.2.1]‐iodomercuri compound 3 yielded the iodides 9, 10, and 11, and iododemercuration of the [3.3.1]‐iodomercuri compound 6 afforded the iodo compounds 9, 11, and 12, respectively. Direct treatment of 4‐cycloocten‐1‐ol (1) with iodine in chloroform resulted in the exclusive formation of the two endo‐iodides 9 and 11.Raney nickel treatment as well as lithium aluminium hydride reduction of each índividual iodo compound 9, 10, 11, and 12 gave the corresponding unsubstituted 9‐oxabicyclononane (4 or 8, respectively) with the unaltered skeleton. No rearrangement products could be observed.An oxonium ion is involved as an intermediate in the reaction of the endo‐iodides 9 and 11 with silver acetate leading to an identical mixture of the two acetates 15 and 16 as well as in the isomerization of 9 to 11.
Published Version
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