期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 15, 页码 10608-10620出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01258
关键词
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资金
- Fundacao para a Ciencia e Tecnologia (FCT), Portugal [UID/MULTI/04326/2019, UIDB/00313/2020, UIDB/00100/2020]
- operational programmes CRESC Algarve 2020 and COMPETE 2020 through project EMBRC.PT [ALG-01-0145-FEDER-022121]
- FCT [SFRH/BD/130407/2017]
- Scientific Employment Stimulus [2020/02383/CEECIND]
- [IST-ID/115/2018]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/130407/2017] Funding Source: FCT
A novel protocol for the synthesis of nonsymmetrical 1,2,4,5-tetraoxanes and 1,2,4-trioxanes using heterogeneous silica sulfuric acid (SSA) catalyst has been reported. The method involves different ketones reacting under mild conditions to generate corresponding endoperoxides in good yields, with the assistance of molecular orbital calculations. This approach provides a valid alternative for the synthesis of new biologically active endoperoxides using readily available and inexpensive reagents with recyclable properties.
A novel protocol for the preparation of nonsymmetrical 1,2,4,5-tetraoxanes and 1,2,4-trioxanes, promoted by the heterogeneous silica sulfuric acid (SSA) catalyst, is reported. Different ketones react under mild conditions with gemdihydroperoxides or peroxysilyl alcohols/beta-hydroperoxy alcohols to generate the corresponding endoperoxides in good yields. Our mechanistic proposal, assisted by molecular orbital calculations, at the.B97XD/def2-TZVPP/PCM(DCM)// B3LYP/6-31G(d) level of theory, enhances the role of SSA in the cyclocondensation step. This novel procedure differs from previously reported methods by using readily available and inexpensive reagents, with recyclable properties, thereby establishing a valid alternative approach for the synthesis of new biologically active endoperoxides.
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