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Diels-Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds.

ABSTRACT: Diels-Alder reactions between cyclopentadiene analogs and p-benzoquinone were explored in water and yielded 83-97% product, higher than the results reported in water with a catalyst or cetrimonium bromide (CTAB) micelles. The novel adduct 10 was synthesized and further used to synthesize the bi-cage hydrocarbon 4,4'-spirobi[pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane], which has a high density (1.2663 g cm^-3) and a high volumetric heat of combustion (53.353 MJ L^-1). Four novel bi-cage hydrocarbon compounds were synthesized in water using this method starting from 2,2'-bi(p-benzoquinone) and cyclopentadiene analogs.

SUBMITTER: Shi Y

PROVIDER: S-EPMC9048223 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Diels-Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds.

Shi Yijun Y Liu Xuejing X Han Ying Y Yan Peng P Bie Fusheng F Cao Han H

RSC advances 20200102 2

Diels-Alder reactions between cyclopentadiene analogs and p-benzoquinone were explored in water and yielded 83-97% product, higher than the results reported in water with a catalyst or cetrimonium bromide (CTAB) micelles. The novel adduct 10 was synthesized and further used to synthesize the bi-cage hydrocarbon 4,4'-spirobi[pentacyclo[5.4.0.02,6.03,10.05,9]undecane], which has a high density (1.2663 g cm-3) and a high volumetric heat of combusti ...[more]

PMID: 35494451

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