Ring-expansion reaction of 1-hydroperoxy-16-oxabicyclo[10.4.0]hexadecane catalyzed by copper ions: use in the synthesis of 15-pentadecanolide Full article
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Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285 |
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| Output data | Year: 1998, Volume: 47, Number: 6, Pages: 1166-1169 Pages count : 4 DOI: 10.1007/bf02503491 | ||
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Abstract:
A catalytic procedure has been developed for the synthesis of 15-pentadecanolide (1) from readily available 1-hydroperoxy-16-oxabicyclo[10.4.0]hexadecane (2). The method is based on the reaction of hydroperoxide2 with copper acetate (0.15–5 mol.%). Ring expansion occurred as a result of generation of tertiary bicyclohexadecyloxyl radicals4 from hydroperoxide2 under the action of Cu1 ions, β-scission of the radicals accompanied by regioselective cleavage of the bridge bond to form macrocyclic C-centered radicals5, and their oxidation by Cu11 ions to (E)-11- and (E)-12-pentadecen-15-olides (6). The products obtained were converted into 15-pentadecanolide by subsequent catalytic hydrogenation over a Pd catalyst in a yield of more than 90% with respect to hydroperoxide2.
Cite:
Ogibin Y.N.
, Terent'ev A.O.
, Nikishin G.I.
Ring-expansion reaction of 1-hydroperoxy-16-oxabicyclo[10.4.0]hexadecane catalyzed by copper ions: use in the synthesis of 15-pentadecanolide
Russian Chemical Bulletin. 1998. V.47. N6. P.1166-1169. DOI: 10.1007/bf02503491 WOS Scopus OpenAlex
Ring-expansion reaction of 1-hydroperoxy-16-oxabicyclo[10.4.0]hexadecane catalyzed by copper ions: use in the synthesis of 15-pentadecanolide
Russian Chemical Bulletin. 1998. V.47. N6. P.1166-1169. DOI: 10.1007/bf02503491 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000075138600023 |
| Scopus: | 2-s2.0-0032398655 |
| OpenAlex: | W2053095102 |