Journal of Organic Chemistry p. 6024 - 6027 (1990)
Update date:2022-07-29
Topics: Ozonolysis Products Heterocyclic Difunctional Conjugated Cyclodienes C5-C8
Griesbaum, Karl
Jung, In Chang
Mertens, Henri
Ozonolyses of the conjugated C5-C8 cyclodienes 1a-d in methanol, followed by reduction with DMS, have been examined.Monoozonolyses gave the corresponding unsaturated dialdehydes 2e as the primary products.In subsequent reactions, the dialdehydes 2e derived from the monoozonolyses of 1a, 1b, and 1c gave in high yields the heterocyclic compounds 7, 8k, and 9k, respectively.Diozonolyses of 1a-d gave the corresponding dialdehydes 3e as the primary products.In subsequent reactions, the dialdehydes 3e derived from 1b and 1c gave the heterocyclic compounds 8l and 9l, respectively.In addition, aldehydes 2e and 3e undervent partial acetalization reactions with methanol.
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Doi:10.1021/jo9806963
(1998)Doi:10.1016/S0040-4020(01)88366-6
(1990)Doi:10.1002/chem.201003681
(2011)Doi:10.1002/ejoc.201001357
(2011)Doi:10.1016/S0040-4039(00)94713-0
(1990)Doi:10.1246/bcsj.63.1546
(1990)