Electronic control of stereoselectivity. 6. Directionality of singlet oxygen addition to 1, 4-dimethoxynaphthalenes laterally fused to bridged bicyclic systems

LA Paquette, F Bellamy, MC Boehm…

Index: Paquette, Leo A.; Bellamy, Francois; Boehm, Michael C.; Gleiter, Rolf Journal of Organic Chemistry, 1980 , vol. 45, # 24 p. 4913 - 4921

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Citation Number: 26

Abstract

Results Synthesis and Oxidation Studies. The preparation of 5 and 6 involved Diels-Alder addition of 1, 4-naphthoquinone to the appropriate dienes followed by 0-methylation. Catalytic hydrogenation of 5 provided 4. The photooxygenation of 4, 5, and 6a proceeded smoothly in (11)(a) Baker, AD; Mag, DP; Turner, DW J. Chem. SOC. B 1968, 22.(b) Turner, DW; Baker, C.; Baker, DA; Brundle, CR" Molecular Photoelectron Spectroscopy"; Wiley- ...

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1,4-naphthoquinone Structure

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1,4-Methano-1,4-dihydroanthracene-9,10-dione Structure

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1,4-Methanoanthracene-9,10-dione, 1,4,4a,9a-tetrahydro- Structure

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1,4-Methano-1,4-dihydroanthracene-9,10-dione Structure

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1,4-Methano-1,4...

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exo-1,4,4a,9a-tetrahydro-4a,9a-epoxy-1,4-ethano-9,10-anthraquinone Structure

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endo-1,4,4a,9a-...

exo-1,4,4a,9a-tetrahydro-4a,9a-epoxy-1,4-ethano-9,10-anthraquinone Structure

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