The Pagodane Route to Dodecahedranes Scope and Limitation of the Dehydrocyclization Stratagem
摘要:
The stepwise route B from pagodanes to dodecahedranes was completed by double catalytic dehydrocyclization of saturated (alkylated) bisseco precursor substrates (2, 3, 5, 16). Based on pagodane, dodecahedranes (9, 10, 13, 14, 17) were obtained in up to 53% yield. Transannular C,C bond formation at the bisseco stage and partial (C–alkyl) or total (C–OR, C–CO<sub>2</sub>R) removal of substituent groups under the necessarily forcing reaction conditions constituted preparative limitations. Attempts at alternative ring closure methodologies (homo-Norrish type II, homoenolization, carbene insertion) have remained unsuccessful.
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关键词:
Bissecododecahedranes hydrogenolysis catalytic dehydrocyclization Dodecahedranes Cyclizations non-dehydrogenative
DOI:
10.1002/cber.19921250729
被引量:
年份:
1992
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