Proton magnetic resonance spectra of cubane derivatives. 3. Transmission of substituent effects in 4-substituted 1-bromohomocubane derivatives

Edward, John T.; Farrell, P.G.; Langford, Gordon E.

doi:10.1021/jo00431a028

Cited by 4 publications

(2 citation statements)

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“…95 In subsequent work, proton NMR chemical shifts and proton-proton coupling constants in substituted 4bromohomocubanes were found to correlate with the corresponding chemical shifts and coupling constants in cubanes. 97 The results were considered to provide evidence for a "through-space mechanism for both cross-ring coupling and the transmission of substituent effects in these systems". 97 The results of complementary studies of acid dissociation constants of 4substituted cubane-1-carboxylic acids98 were rationalized in terms of the Kirkwood-Westheimer field mod-el99 for propagation of polar substituent effects in saturated systems.…”

Section: Miscellaneous Studies Involving Cubanesmentioning

confidence: 99%

“…97 The results were considered to provide evidence for a "through-space mechanism for both cross-ring coupling and the transmission of substituent effects in these systems". 97 The results of complementary studies of acid dissociation constants of 4substituted cubane-1-carboxylic acids98 were rationalized in terms of the Kirkwood-Westheimer field mod-el99 for propagation of polar substituent effects in saturated systems.…”

Section: Miscellaneous Studies Involving Cubanesmentioning

confidence: 99%

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Synthesis and chemistry of cubanes

Griffin¹,

Marchand²

1989

Chem. Rev.

173

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Section: Miscellaneous Studies Involving Cubanesmentioning

confidence: 99%

Section: Miscellaneous Studies Involving Cubanesmentioning

confidence: 99%

Synthesis and chemistry of cubanes

Griffin¹,

Marchand²

1989

Chem. Rev.

173

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ChemInform Abstract: PROTON MAGNETIC RESONANCE SPECTRA OF CUBANE DERIVATIVES. 3. TRANSMISSION OF SUBSTITUENT EFFECTS IN 4‐SUBSTITUTED 1‐BROMOHOMOCUBANE DERIVATIVES

Edward¹,

Farrell²,

Langford³

1977

Chemischer Informationsdienst

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NMR and conformational studies of the cyclobutane ring involved in the bicyclo [4.2.0]octane system of a tetracyclic diterpene structure

Manh

Fétizon

Prévost

et al. 1991

Magnetic Reson in Chemistry

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Conformational studies were performed on the bicyclo [ 4.2.0 loctane system of a series of related tetracyclic diterpenes, using molecular mechanics and 'H NMR. Both methods gave compatible results, but did not permit the deduction of any quantitative relationship linking the vicinal coupling constants to the cyclobutane dihedral angles. Nevertheless, the Karplus relationship allowed a qualitative interpretation of the coupling constants in terms of conformation. A set of characteristic 'H NMR coupling constants was obtained which allows the interpretation of the 'H NMR spectrum of any compound presenting a similar system. KEY WORDS NMR double irradiation Internal coupling constants of cyclobutane Karplus relationship MM2 calculations Conformational analysis 2H-CycIobutan[jl-5-hydroxy-8,8,1 latrimethyldodcecahydro[3aS-(3aar,5aRZ,7aa,1 la/3,ll ba)]phenanthren-3(3aH)-one Synthesis The synthesis of the series A compounds was described in Ref. 21 for 17, Ref. 22 for 2H-cyclobutanE]-5-hydroxy-8,8,1 l atrimethyldodecahydro[3aS -(3aa,SaR*,7aa,l lab, llba)]phenanthren-3(3aH)one 1, 2, 7, 8, 14 and 19 and Ref. 20 for the others. The compounds were obtained from

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Proton magnetic resonance spectra of cubane derivatives. 3. Transmission of substituent effects in 4-substituted 1-bromohomocubane derivatives

Cited by 4 publications

References 0 publications

Synthesis and chemistry of cubanes

Synthesis and chemistry of cubanes

ChemInform Abstract: PROTON MAGNETIC RESONANCE SPECTRA OF CUBANE DERIVATIVES. 3. TRANSMISSION OF SUBSTITUENT EFFECTS IN 4‐SUBSTITUTED 1‐BROMOHOMOCUBANE DERIVATIVES

NMR and conformational studies of the cyclobutane ring involved in the bicyclo [4.2.0]octane system of a tetracyclic diterpene structure

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