A hydrogen atom sandwiched by cyclopropanes

Compound 1 was synthesized in four steps from 1,3-dibromobenzene. The X-ray crystal structure of 1 shows that H 9 is located approximately 2.6 Å from the centroids of each of the flanking cyclopropane rings, and its proton NMR resonance falls 0.84 ppm upfield from the resonance of the otherwise chem...

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Bibliographic Details
Published in:Tetrahedron letters 2005-09, Vol.46 (38), p.6487-6489
Main Authors: Walters, Robert S., Ho, Douglas M., Pascal, Robert A.
Format: Article
Language:English
Subjects:
Cyclopropane
Magnetic anisotropy
NMR
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Summary:Compound 1 was synthesized in four steps from 1,3-dibromobenzene. The X-ray crystal structure of 1 shows that H 9 is located approximately 2.6 Å from the centroids of each of the flanking cyclopropane rings, and its proton NMR resonance falls 0.84 ppm upfield from the resonance of the otherwise chemically similar H 10. 2′,3′,4′,5′,6′,7′-Hexahydrodispiro[cyclopropane-1,1′-anthracene-8′,1″-cyclopropane] ( 1 ) was prepared by double olefination (Wittig) and double methylenation (Furukawa) of 1,8-dioxo-1,2,3,4,5,6,7,8-octahydroanthracene ( 4 ) that was in turn prepared in two steps from 1,3-dibromobenzene. The X-ray structure of 1 shows that the C–9-H of its anthracene core is located 2.6 Å from the centroids of each of the flanking cyclopropane rings. The 1H NMR spectrum of 1 shows that the C–9-H resonance ( δ 5.95) falls 0.84 ppm upfield from the C–10-H resonance ( δ 6.79).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.07.097