Bifunctional Derivatives of 2,6-Dimethylnaphthalene.

Taussig, P. R.; Storms, Phillip W.

doi:10.1021/je60029a049

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Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the ¹³C chemical shifts with the aid of deuterated derivatives

1978

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Proton-coupled as well as noise-decoupled '"C NMR spectra of several substituted naphthalenes have been studied. Complete assignments of the ' " C signals based on selectively deuterated derivatives and on the '"C-'H coupling pattern have been made. For the methoxynaphthalenes, acetylnaphthalenes and naphthaldehydes the dominant conformations of the substituents have been deduced from the '"C chemical shifts.

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Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the ¹³C chemical shifts with the aid of deuterated derivatives

1978

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Carbon‐13 NMR studies of substituted naphthalenes. II—rotational barriers and conformations in some naphthaldehydes and azulenaldehydes

Drakenberg¹,

Sandström²,

Seita³

1978

Org. Magn. Reson.

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Proton-coupled and noise-decoupled "C NMR spectra of 1-azulenecnrbaldehyde, 1-acetylazulene and 1,3-azulenedicarbaldehyde have been studied, and complete assignments have been made based on the C-'H coupling constants, additivity of substitoent effects (SIS), and previous assignment for the parent hydrocarbon. The barriers to rotation of the aldehyde group in the above azuleneaubaldehydes and in some naphthaldehydes have been determined by -C dynamic NMR, (DNMR), resulting in free energies of activation of 42.7, 26.8 and 34.4W m0l-l for 1-azulenecarbaldehyde, 1-naphthaldehyde and 2-naphthaldehyde respectively. The same order of barriers is obtained by -012 calculations. A 4-metbxy substitoent in 1-naphthaldehyde and a 6-methoxy substituent in 2-naphthaldehyde increases the rotational barrier by 4.6 and 2.9 W mol-', respectively, whereas a d-methoxy substituent in 2-naphthaldehyde reduces the barrier by 6.7W mol-'. The conformatiom of the dominant rotamers are deduced from -C chemical shifts to be 2 for 1-azuleneuubaldehyde and 1-napbthaldehyde, and E for 2-naphthaldehyde. 13

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Aromatic and heteroaromatic compounds by electrocyclic ring-closure with elimination

Jutz

Organic Chemistry

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Bifunctional Derivatives of 2,6-Dimethylnaphthalene.

Cited by 5 publications

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Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the ¹³C chemical shifts with the aid of deuterated derivatives

Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the ¹³C chemical shifts with the aid of deuterated derivatives

Carbon‐13 NMR studies of substituted naphthalenes. II—rotational barriers and conformations in some naphthaldehydes and azulenaldehydes

Aromatic and heteroaromatic compounds by electrocyclic ring-closure with elimination

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Bifunctional Derivatives of 2,6-Dimethylnaphthalene.

Cited by 5 publications

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Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the 13C chemical shifts with the aid of deuterated derivatives

Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the 13C chemical shifts with the aid of deuterated derivatives

Carbon‐13 NMR studies of substituted naphthalenes. II—rotational barriers and conformations in some naphthaldehydes and azulenaldehydes

Aromatic and heteroaromatic compounds by electrocyclic ring-closure with elimination

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Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the ¹³C chemical shifts with the aid of deuterated derivatives

Carbon‐13 NMR studies of substituted naphthalenes. I—complete assignments of the ¹³C chemical shifts with the aid of deuterated derivatives