Tetracyclo[4.1.0.02,4.03,5]heptanes from 7,8‐Diazatetracyclo[4.3.0.02,4.03,5]non‐7‐enes

Christl, Manfred; Brunn, Erich

doi:10.1002/anie.198104681

Cited by 5 publications

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“…The size of the shielding effects in the bicyclo[1.1.0]butane system of 27 seems to indicate an electron donation by the oxygen atom. Similar, although smaller, influences are observed upon substitution of the H-7exo of 1 with a fluorine atom as in 48.13 Since the unoccupied Walsh orbitals (36) of fluorocyclopropane (X = CHF, E = 2.17 eyi5b,c) an<¿ thiirane S-oxide (X = SO, E = -0.12 eV15b) have lower energies than those of cyclopropane and thiirane, respectively (vide supra), the interaction 35 should be improved in 27 and 48 relative to that of 26 respectively. Consequently, the C-3 resonances of 27 and 48 should appear downfield from those of 26 and 1, respectively.…”

Section: Resultsmentioning

confidence: 99%

Carbon-13 nuclear magnetic resonance spectra of 7-heterotetracyclo[4.1.0.02,4.03,5]heptanes. Annelation effects of aziridine, oxirane, and thiirane rings. Unusual .gamma. and .delta. substituent effects

Christl¹,

Leininger²,

Brunn³

1982

J. Org. Chem.

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The 18C NMR spectra of 7-heterotetracyclo[4.1.0.02.'.08.5]heptanes and of the 7-methyl-and 7-phenyltetracyclo[4.1.0.0U.os.&]heptanea have been measured, and the three-membered-ring annelation effects were determined. The unusual deahielding found for the C-3 resonance in a cyclopropane-annelated cyclopentane derivative (bicyclo[3.1.0]hexane derivative) in the chair conformation carries an even stronger effect in the analogous aziridine-, omene-, and thiirane-annelated systems. Substituents in the 7-poeition oftetracyclo

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Section: Resultsmentioning

confidence: 99%